Aromatic amine derivative and organic electroluminescence device employing the same

ABSTRACT

A specified aromatic amine derivative having a chrysene structure. An organic electroluminescence device which comprises at least one organic thin film layer comprising a light emitting layer sandwiched between a pair of electrode consisting of an anode and a cathode, wherein at least one of the organic thin film layer comprises the aromatic amine derivative singly or as its mixture component. Organic electroluminescence devices having a long lifetime and a high efficiency of light emission, and aromatic amine derivatives capable of realizing such organic electroluminescence devices are provided.

TECHNICAL FIELD

The present invention relates to an aromatic amine derivative and anorganic electroluminescence device using the derivative and, moreparticularly, to an organic electroluminescence device having longlifetime, an enhanced efficiency of light emission and emitting highlypure blue light; and to an aromatic amine derivative realizing theorganic electroluminescence device.

BACKGROUND ART

Organic electroluminescence (“electroluminescence” will be occasionallyreferred to as “EL”, hereinafter) devices which utilize organicsubstances are expected to be useful for application as an inexpensivefull color display device of the solid light emission type having agreat size and various developments on the organic EL devices are beingconducted. In general, an organic EL device has a constructioncomprising a light emitting layer and a pair of electrodes sandwichingthe light emitting layer. The light emission of the organic EL device isa phenomenon in which, when an electric field is applied between the twoelectrodes, electrons are injected from the cathode side and holes areinjected from the anode side, the electrons are recombined with theholes in the light emitting layer to form an excited state, and energygenerated when the excited state returns to the ground state is emittedas light.

As compared with an inorganic light emitting diode, conventional organicEL devices requires high driving voltage and only exhibited lowluminance or low efficiency of light emission. Moreover, characteristicdegradation of the conventional organic EL devices was also extravagantand as a result, they were not practically used. Although recent organicEL devices are improved step by steps, it has been still demanded todevelop organic EL devices with favorable efficiency of light emissionand having long lifetime.

For example, there is disclosed such a technique using a singlemonoanthracene compound as an organic light-emitting material (refer toPatent Literature 1 below). However, in this technique, a luminanceobtained by using the material is as low as 1650 cd/m², for example, ata current density of 165 mA/cm², and an efficiency of light emissionthereof is very low, i.e., only 1 cd/A, which is practically unusable.Also, there is disclosed a technique using a single bisanthracenecompound as an organic light emitting material (refer to PatentLiterature 2 below). However, in this technique, an efficiency of lightemission obtained by using the material is also as low as about 1 to 3cd/A. Therefore, further improvement of the technique has bee demandedfor rendering it practically usable. Further, there is disclosed atechnique using a distyryl compound and adding styrylamine or so asorganic light emitting material (refer to Patent Literature 3 below).However, the device described therein fails to show a sufficiently longlifetime and, therefore, further improvement has been demanded.

Furthermore, a technique of employing mono- or bis-anthracene compoundand a distyryl compound as an organic light emitting medium layer isdisclosed (refer to Patent Literature 4 below). However in thesetechnologies, a conjugated structure of the styryl compound lengthenedwave length of a light emission spectrum and deteriorated the purity ofcolor.

Still further, Patent Literature 5 below discloses a blue luminescencedevice with the use of diaminochrysene derivatives. However, despite thesuperiority in light emission efficiency, because the device is notsufficient in its lifetime, further improvement was required.

-   -   Patent Literature 1: Japanese Unexamined Patent Application        Laid-Open No. Hei 11-3782A    -   Patent Literature 2: Japanese Unexamined Patent Application        Laid-Open No. Hei 8(1996)-012600    -   Patent Literature 3: International Patent Application Published        under PCT No. WO 00/06402    -   Patent Literature 4: Japanese Unexamined Patent Application        Laid-Open No. 2001-284050    -   Patent Literature 5: International Application Published under        PCT No. WO 04/04088

DISCLOSURE OF THE INVENTION

The present invention has been made to overcome the above problems. Anobject of the present invention is to provide organic EL devices havinga long lifetime and a high efficiency of light emission, and aromaticamine derivatives capable of realizing such organic EL devices.

As a result of extensive researches for developing aromatic aminederivatives having the above suitable properties and organic EL devicesusing the aromatic amine derivatives, the inventors have found that theobject of the present invention can be achieved by using aromatic aminederivatives represented by a following general formula (1) or (2) inwhich an amino group is bonded to a substituted chrysene structure. Thepresent invention has been accomplished on the basis of the abovefinding.

Namely, the present invention provides an aromatic amine derivativerepresented by the following general formula (1) or general formula (2):

In the general formula (1), A₁ to A₄ each independently represents ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted aryl group having 5 to 50ring carbon atoms, a substituted or unsubstituted aralkyl group having 1to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxylgroup having 1 to 50 carbon atoms, a substituted or unsubstitutedaryloxy group having 5 to 50 ring carbon atoms, a substituted orunsubstituted arylamino group having 5 to 50 ring carbon atoms, asubstituted or unsubstituted alkylamino group having 1 to 20 carbonatoms, a substituted or unsubstituted heterocyclic group having 3 to 50ring carbon atoms, a substituted or unsubstituted silyl group having 3to 50 carbon atoms or a halogen atom;

-   a, b, c and d each independently represents an integer of 0 to 5,    when a, b, c or d each is 2 or greater, A₁ to A₄ may be the same    with or different from each other, and may bond each other to form a    saturated or unsaturated ring; and further, a couple of A₁ and A₂,    and a couple of A₃ and A₄ may bond each other to form a saturated or    unsaturated ring;-   R₁ to R₄ each independently represents a hydrogen atom, a    substituted or unsubstituted alkyl group having 1 to 50 carbon    atoms, a substituted or unsubstituted aryl group having 5 to 50 ring    carbon atoms, a substituted or unsubstituted aralkyl group having 6    to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl    group having 3 to 50 ring carbon atoms, a substituted or    unsubstituted arylamino group having 5 to 20 ring carbon atoms, a    substituted or unsubstituted alkylamino group having 1 to 20 carbon    atoms, a substituted or unsubstituted heterocyclic group having 3 to    50 ring carbon atoms or a substituted or unsubstituted silyl group    having 3 to 50 carbon atoms; a couple of R₁ and R₂, and a couple of    R₃ and R₄ may bond each other to form a saturated or unsaturated    ring.

However, a case where all of R₁ to R₄ in the general formula (1) arehydrogen atoms is excluded.

In the general formula (2), A₅ to A₈ each independently represents asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted aryl group having 5 to 50 ring carbonatoms, a substituted or unsubstituted cycloalkyl group having 3 to 50ring carbon atoms or a substituted or unsubstituted heterocyclic grouphaving 3 to 50 ring carbon atoms;

-   R₅ to R₈ each independently represents a hydrogen atom, a    substituted or unsubstituted alkyl group having 1 to 50 carbon    atoms, a substituted or unsubstituted aryl group having 5 to 50 ring    carbon atoms, a substituted or unsubstituted aralkyl group having 6    to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl    group having 3 to 50 ring carbon atoms, a substituted or    unsubstituted arylamino group having 5 to 20 ring carbon atoms, a    substituted or unsubstituted alkylamino group having 1 to 20 carbon    atoms or a substituted or unsubstituted heterocyclic group having 3    to 50 ring carbon atoms; and a couple of R₅ and R₆, and a couple of    R₇ and R₈ may bond each other to form a saturated or unsaturated    ring.

Further, the present invention provides an organic EL device whichcomprises at least one organic thin film layer comprising a lightemitting layer sandwiched between a pair of electrode consisting of ananode and a cathode, wherein at least one of the organic thin filmlayers comprises the aromatic amine derivative singly or as its mixturecomponent.

The organic EL device employing the aromatic amine derivative of thepresent invention reveals practically sufficient luminance even underlow applied voltage, exhibits an enhanced efficiency of light emission,and is resistant to degrade even after a long time usage demonstrating aprolonged lifetime.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a chart showing a result of ¹H-NMR measurement about Compound(4) obtained in Synthesis Example 1;

FIG. 2 is a chart showing a result of ¹H-NMR measurement about Compound(9) obtained in Synthesis Example 2;

FIG. 3 is a chart showing a result of ¹H-NMR measurement about Compound(20) obtained in Synthesis Example 3;

FIG. 4 is a chart showing a result of ¹H-NMR measurement about Compound(23) obtained in Synthesis Example 4;

FIG. 5 is a chart showing a result of ¹H-NMR measurement about Compound(25) obtained in Synthesis Example 5;

FIG. 6 is a chart showing a result of ¹H-NMR measurement about Compound(39) obtained in Synthesis Example 6;

FIG. 7 is a chart showing a result of ¹H-NMR measurement about Compound(57) obtained in Synthesis Example 7;

FIG. 8 is a chart showing a result of ¹H-NMR measurement about Compound(95) obtained in Synthesis Example 8;

FIG. 9 is a chart showing a result of ¹H-NMR measurement about Compound(D-973) obtained in Synthesis Example 9;

FIG. 10 is a chart showing a result of ¹H-NMR measurement about Compound(D-974) obtained in Synthesis Example 10;

FIG. 11 is a chart showing a result of ¹H-NMR measurement about Compound(D-998) obtained in Synthesis Example 11; and

FIG. 12 is a chart showing a result of ¹H-NMR measurement about Compound(D-1000) obtained in Synthesis Example 12;

THE PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

The present invention provides an aromatic amine derivative representedby a following general formula (1) or a general formula (2):

First, the aromatic amine derivative represented by the general formula(1) will be explained below.

In the general formula (1), A₁ to A₄ each independently represents ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50(preferably 1 to 20) carbon atoms, a substituted or unsubstituted arylgroup having 5 to 50 (preferably 5 to 20) ring carbon atoms, asubstituted or unsubstituted aralkyl group having 1 to 50 (preferably 6to 20) ring carbon atoms, a substituted or unsubstituted cycloalkylgroup having 3 to 50 (preferably 5 to 12) ring carbon atoms, asubstituted or unsubstituted alkoxyl group having 1 to 50 (preferably 1to 6) carbon atoms, a substituted or unsubstituted aryloxy group having5 to 50 (preferably 5 to 18) ring carbon atoms, a substituted orunsubstituted arylamino group having 5 to 50 (preferably 5 to 18) ringcarbon atoms, a substituted or unsubstituted alkylamino group having 1to 20 (preferably 1 to 6) carbon atoms, a substituted or unsubstitutedheterocyclic group having 3 to 50 (preferably 3 to 20) ring carbonatoms, a substituted or unsubstituted silyl group having 3 to 50(preferably 3 to 20) carbon atoms or a halogen atom.

Examples of the substituted or unsubstituted alkyl group represented byA₁ to A₄ include methyl group, ethyl group, propyl group, isopropylgroup, butyl group, sec-butyl group, tert-butyl group, pentyl group,hexyl group, heptyl group, octyl group, stearyl group, trichloromethylgroup, trifluoromethyl group, etc.

Examples of the substituted or unsubstituted aryl group represented byA₁ to A₄ include phenyl group, 2-methylphenyl group, 3-methylphenylgroup, 4-methylphenyl group, 4-ethylphenyl group, biphenyl group,4-methylbiphenyl group, 4-ethylbiphenyl group, 4-cyclohexylbiphenylgroup, terphenyl group, 3,5-dichlorophenyl group, naphthyl group,5-methylnaphthyl group, anthryl group, pyrenyl group, etc.

Examples of the substituted or unsubstituted aralkyl group representedby A₁ to A₄ include benzyl group, α,α-methylphenylbenzyl group,triphenylmethyl group, 1-phenylethyl group, 2-phenylethyl group,1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group,-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethy group,1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group,β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethylgroup, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group,α-phenoxybenzyl group, α-benzyloxy benzyl group,α,α-ditrifluoromethylbenzyl group, 1-pyrrolylmethyl group,2-(1-pyrrolyl)ethyl, p-methylbenzyl group, m-methylbenzyl group,o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group,o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group,o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group,o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group,o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group,o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group,o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group,o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group and1-chloro-2-phenylisopropyl group, etc.

Examples of the cycloalkyl group represented by A₁ to A₄ includecyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexylgroup, etc.

Examples of the alkoxy group represented by A₁ to A₄ include methoxygroup, ethoxy group, propoxy group, isopropoxy group, butoxy group,isobutoxy group, s-butoxy group, t-butoxy group, various pentyloxygroups, various hexyloxy groups, etc.

Examples of the aryloxy group represented by A₁ to A₄ include phenoxygroup, tolyloxy group, naphthyloxy group, etc.

Examples of the arylamino group represented by A₁ to A₄ includediphenylamino group, ditolylamino group, isopropyldiphenylamino group,t-butyldiphenylamino group, diisopropyldiphenylamino group,di-t-butyldiphenylamino group, dinaphthylamino group,naphthylphenylamino group, etc.

Examples of the alkylamino group represented by A₁ to A₄ includedimethylamino group, diethylamino group, dihexylamino group, etc.

Examples of the heterocyclic group represented by A₁ to A₄ includemoieties of imidazole, benzimidazole, pyrrole, furan, thiophene,benzothiophene, oxadi azoline, indoline, carbazole, pyridine, quinoline,isoquinoline, benzoquinone, pyrazoline, imidazolidine, piperidine, etc.

Examples of the substituted or unsubstituted silyl group represented byA₁ to A₄ include trimethylsilyl group, triethylsilyl group,t-butyldimethylsilyl group, vinyldimethylsilyl group,propyldimethylsilyl group, methyldiphenylsilyl group,dimethylphenylsilyl group, triphenylsilyl group), etc.

Examples of the halogen atom represented by A₁ to A₄ include fluorineatom, chlorine atom, bromine atom, etc.

In the general formula (1), a, b, c and d each independently representsan integer of 0 to 5, preferably an integer of 0 to 3, and morepreferably an integer of 0 to 2.

When a, b, c or d each is 2 or greater, A₁ to A₄ may be the same with ordifferent from each other, and may bond each other to form a saturatedor unsaturated ring; and further, a couple of A₁ and A₂, and a couple ofA₃ and A₄ may bond each other to form a saturated or unsaturated ring;

Examples of the ring include cycloalkane having 4 to 12 carbon atomssuch as cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane,etc.; cycloalkene having 4 to 12 carbon atoms such as cyclobutene,cyclopentene, cyclohexene, cyclo heptene, cyclo octene, etc.;cycloalkadiene having 6 to 12 carbon atoms such as cyclohexa diene,cyclohepta diene, cyclo octadiene, etc.; aromatic ring having 6 to 50carbon atoms such as benzene, naphthalene, phenanthrene, anthracene,pyrene, chrysene, acenaphthylene, etc.; and the like.

In the general formula (1), R₁ to R₄ each independently represents ahydrogen atom, a substituted or unsubstituted alkyl group (preferably aprimary or a secondary alkyl group) having 1 to 50 (preferably 1 to 20)carbon atoms, a substituted or unsubstituted aryl group having 5 to 50(preferably 5 to 20) ring carbon atoms, a substituted or unsubstitutedaralkyl group having 6 to 50 (preferably 6 to 20) ring carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 50 (preferably5 to 12) ring carbon atoms, a substituted or unsubstituted arylaminogroup having 5 to 20 (preferably 5 to 18) ring carbon atoms, asubstituted or unsubstituted alkylamino group having 1 to 20 (preferably1 to 10) carbon atoms, a substituted or unsubstituted heterocyclic grouphaving 3 to 50 (preferably 3 to 20) ring carbon atoms, a substituted orunsubstituted silyl group having 3 to 50 (preferably 3 to 20) carbonatoms; a couple of R₁ and R₂, and a couple of R₃ and R₄ may bond eachother to form a saturated or unsaturated ring.

Specific examples of the substituted or unsubstituted alkyl group, arylgroup, aralkyl group, cycloalkyl group, arylamino group, alkylaminogroup, heterocyclic group, silyl group and the saturated or unsaturatedring represented by R₁ to R₄ are the same as those exemplified as A₁ toA₄ above.

It is particularly preferable that the alkyl group represented by R₂ andR₄ are primary or secondary.

Further, examples of the substituent for A₁ to A₄ and R₁ to R₄ include asubstituted or unsubstituted aryl group having 5 to 50 (preferably 5 to20) ring carbon atoms, a substituted or unsubstituted alkyl group having1 to 50 (preferably 1 to 20) carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 50 (preferably 1 to 20) carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 50(preferably 6 to 20) ring carbon atoms, a substituted or unsubstitutedaryloxy group having 5 to 50 (preferably 5 to 20) ring carbon atoms, asubstituted or unsubstituted arylthio group having 5 to 50 (preferably 5to 20) ring carbon atoms, a substituted or unsubstituted alkoxycarbonylgroup having 1 to 50 (preferably 1 to 20) carbon atoms, amino group,halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group,etc.

However, a case where all of R₁ to R₄ in the general formula (1) arehydrogen atoms is excluded.

Further in the general formula (1), it is preferable that R₁ and/or R₃independently represents a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted aryl grouphaving 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkylgroup having 6 to 50 ring carbon atoms or a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms. It is preferable thatR₁ and R₃ each independently represents a substituted or unsubstitutedalkyl group having 1 to 50 carbon atoms, a substituted or unsubstitutedaryl group having 5 to 50 ring carbon atoms, a substituted orunsubstituted aralkyl group having 6 to 50 ring carbon atoms or asubstituted or unsubstituted cycloalkyl group having 3 to 50 ring carbonatoms.

Still further in the general formula (1), it is preferable that R₁ to R₄each independently represents a hydrogen atom, a substituted orunsubstituted arylamino group having 5 to 20 ring carbon atoms, asubstituted or unsubstituted alkylamino group having 1 to 20 carbonatoms, a substituted or unsubstituted heterocyclic group having 5 to 50ring carbon atoms or a substituted or unsubstituted silyl group having 3to 50 carbon atoms.

Further, it is preferable that R₁ and/or R₃ represents a methyl group,an ethyl group, a propyl group, an isopropyl group, a butyl group, as-butyl group, a t-butyl group or a cyclohexyl group.

Furthermore, it is preferable that R₂ and/or R₄ represents a methylgroup, an ethyl group, a propyl group, an isopropyl group, a butylgroup, a s-butyl group, a t-butyl group or a cyclohexyl group.

Next, the aromatic amine derivative represented by the general formula(2) will be explained below.

In the general formula (2), A₅ to A₈ each independently represents ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50(preferably 1 to 20) carbon atoms, a substituted or unsubstituted arylgroup having 5 to 50 (preferably 5 to 20) ring carbon atoms, asubstituted or unsubstituted cycloalkyl group having 3 to 50 (preferably5 to 12) ring carbon atoms or a substituted or unsubstitutedheterocyclic group having 3 to 50 (preferably 3 to 20) ring carbonatoms;

In the general formula (2), R₅ to R₈ each independently represents ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50(preferably 1 to 20) carbon atoms, a substituted or unsubstituted arylgroup having 5 to 50 (preferably 5 to 20) ring carbon atoms, asubstituted or unsubstituted aralkyl group having 6 to 50 (preferably 6to 20) ring carbon atoms, a substituted or unsubstituted cycloalkylgroup having 3 to 50 (preferably 5 to 12) ring carbon atoms, asubstituted or unsubstituted arylamino group having 5 to 20 (preferably5 to 12) ring carbon atoms, a substituted or unsubstituted alkylaminogroup having 1 to 20 (preferably 1 to 10) carbon atoms or a substitutedor unsubstituted heterocyclic group having 3 to 50 (preferably 3 to 20)ring carbon atoms; a couple of R₅ and R₆, and a couple of R₇ and R₈ maybond each other to form a saturated or unsaturated ring.

Specific examples of the groups represented by A₅ to A₈ and R₅ to R₈ inthe general formula (2), specific examples of those substituent andspecific examples of those saturated or unsaturated ring are the same asthose exemplified as A₁ to A₄ and R₁ to R₄ in the foregoing generalformula (1).

Specific examples of the aromatic amine derivatives represented by thegeneral formula (1) or the general formula (2) will be illustratedbelow, though not particularly limited thereto. Meanwhile, in thefollowing compounds, Me represents a methyl group.

TABLE 1 R₁ R₂ R₃ R₄

D-1 Methyl H H H

D-2 Methyl H H H

D-3 Methyl H H H

D-4 Methyl H H H

D-5 Methyl H H H

D-6 Methyl H H H

D-7 Methyl H H H

D-8 Methyl H H H

D-9 Methyl H H H

D-10 Methyl H H H

D-11 Methyl H H H

D-12 Methyl H H H

TABLE 2     R₁     R₂     R₃     R₄

D-13 Methyl H H H

D-14 Methyl H H H

D-15 Methyl H H H

D-16 Methyl H H H

D-17 Methyl H H H

D-18 Methyl H H H

D-19 Methyl H H H

D-20 Methyl H H H

D-21 Methyl H H H

D-22 Methyl H H H

D-23 Methyl H H H

D-24 Methyl H H H

TABLE 3     R₁     R₂     R₃     R₄

D-25 Methyl H H H

D-26 Methyl H H H

D-27 Methyl H H H

D-28 Methyl H H H

D-29 Methyl H H H

D-30 Methyl H H H

D-31 Methyl H H H

D-32 Methyl H H H

D-33 Methyl H H H

D-34 Methyl H H H

D-35 Methyl H H H

D-36 Methyl H H H

TABLE 4     R₁     R₂     R₃     R₄

D-37 Methyl H H H

D-38 Methyl H H H

D-39 Methyl H H H

D-40 Methyl H H H

D-41 Methyl H H H

D-42 Methyl H H H

D-43 Methyl H H H

D-44 Methyl H H H

D-45 Methyl H H H

D-46 Methyl H H H

D-47 Methyl H H H

D-48 Methyl H H H

TABLE 5     R₁     R₂     R₃     R₄

D-49 Iso-pro-pyl H H H

D-50 Iso-pro-pyl H H H

D-51 Iso-pro-pyl H H H

D-52 Iso-pro-pyl H H H

D-53 Iso-pro-pyl H H H

D-54 Iso-pro-pyl H H H

D-55 Iso-pro-pyl H H H

D-56 Iso-pro-pyl H H H

D-57 Iso-pro-pyl H H H

D-58 Iso-pro-pyl H H H

D-59 Iso-pro-pyl H H H

D-60 Iso-pro-pyl H H H

TABLE 6     R₁     R₂     R₃     R₄

D-61 Isopropyl H H H

D-62 Isopropyl H H H

D-63 Isopropyl H H H

D-64 Isopropyl H H H

D-65 Isopropyl H H H

D-66 Isopropyl H H H

D-67 Isopropyl H H H

D-68 Isopropyl H H H

D-69 Isopropyl H H H

D-70 Isopropyl H H H

D-71 Isopropyl H H H

D-72 Isopropyl H H H

TABLE 7     R₁     R₂     R₃     R₄

D-73 Isopropyl H H H

D-74 Isopropyl H H H

D-75 Isopropyl H H H

D-76 Isopropyl H H H

D-77 Isopropyl H H H

D-78 Isopropyl H H H

D-79 Isopropyl H H H

D-80 Isopropyl H H H

D-81 Isopropyl H H H

D-82 Isopropyl H H H

D-83 Isopropyl H H H

D-84 Isopropyl H H H

TABLE 8     R₁     R₂     R₃     R₄

D-85 Isopropyl H H H

D-86 Isopropyl H H H

D-87 Isopropyl H H H

D-88 Isopropyl H H H

D-89 Isopropyl H H H

D-90 Isopropyl H H H

D-91 Isopropyl H H H

D-92 Isopropyl H H H

D-93 Isopropyl H H H

D-94 Isopropyl H H H

D-95 Isopropyl H H H

D-96 Isopropyl H H H

TABLE 9   R₁   R₂   R₃   R₄

D-97 t-butyl H H H

D-98 t-butyl H H H

D-99 t-butyl H H H

D-100 t-butyl H H H

D-101 t-butyl H H H

D-102 t-butyl H H H

D-103 t-butyl H H H

D-104 t-butyl H H H

D-105 t-butyl H H H

D-106 t-butyl H H H

D-107 t-butyl H H H

D-108 t-butyl H H H

TABLE 10     R₁     R₂     R₃     R₄

D-109 t-butyl H H H

D-110 t-butyl H H H

D-111 t-butyl H H H

D-112 t-butyl H H H

D-113 t-butyl H H H

D-114 t-butyl H H H

D-115 t-butyl H H H

D-116 t-butyl H H H

D-117 t-butyl H H H

D-118 t-butyl H H H

D-119 t-butyl H H H

D-120 t-butyl H H H

TABLE 11     R₁     R₂     R₃     R₄

D-121 t-butyl H H H

D-122 t-butyl H H H

D-123 t-butyl H H H

D-124 t-butyl H H H

D-125 t-butyl H H H

D-126 t-butyl H H H

D-127 t-butyl H H H

D-128 t-butyl H H H

D-129 t-butyl H H H

D-130 t-butyl H H H

D-131 t-butyl H H H

D-132 t-butyl H H H

TABLE 12     R₁     R₂     R₃     R₄

D-133 t-butyl H H H

D-134 t-butyl H H H

D-135 t-butyl H H H

D-136 t-butyl H H H

D-137 t-butyl H H H

D-138 t-butyl H H H

D-139 t-butyl H H H

D-140 t-butyl H H H

D-141 t-butyl H H H

D-142 t-butyl H H H

D-143 t-butyl H H H

D-144 t-butyl H H H

TABLE 13     R₁     R₂     R₃     R₄

D-145 Phenyl H H H

D-146 Phenyl H H H

D-147 Phenyl H H H

D-148 Phenyl H H H

D-149 Phenyl H H H

D-150 Phenyl H H H

D-151 Phenyl H H H

D-152 Phenyl H H H

D-153 Phenyl H H H

D-154 Phenyl H H H

D-155 Phenyl H H H

D-156 Phenyl H H H

TABLE 14     R₁     R₂     R₃     R₄

D-157 1-naphtyl H H H

D-158 1-naphtyl H H H

D-159 1-naphtyl H H H

D-160 1-naphtyl H H H

D-161 1-naphtyl H H H

D-162 1-naphtyl H H H

D-163 1-naphtyl H H H

D-164 1-naphtyl H H H

D-165 1-naphtyl H H H

D-166 1-naphtyl H H H

D-167 1-naphtyl H H H

D-168 1-naphtyl H H H

TABLE 15     R₁     R₂     R₃     R₄

D-169 2-naphtyl H H H

D-170 2-naphtyl H H H

D-171 2-naphtyl H H H

D-172 2-naphtyl H H H

D-173 2-naphtyl H H H

D-174 2-naphtyl H H H

D-175 2-naphtyl H H H

D-176 2-naphtyl H H H

D-177 2-naphtyl H H H

D-178 2-naphtyl H H H

D-179 2-naphtyl H H H

D-180 2-naphtyl H H H

TABLE 16     R₁     R₂     R₃     R₄

D-181 Cyano H H H

D-182 Cyano H H H

D-183 Dimethylamino H H H

D-184 Dimethylamino H H H

D-185 Dimethylamino H H H

D-186 2-methylphenyl H H H

D-187 2-methylphenyl H H H

D-188 2-methylphenyl H H H

D-189 2-biphenyl H H H

D-190 2-biphenyl H H H

D-191 2-biphenyl H H H

D-192 2-biphenyl H H H

TABLE 17     R₁     R₂     R₃     R₄

D-193 Methyl Methyl H H

D-194 Methyl Methyl H H

D-195 Methyl Methyl H H

D-196 Methyl Methyl H H

D-197 Methyl Methyl H H

D-198 Methyl Methyl H H

D-199 Methyl Methyl H H

D-200 Methyl Methyl H H

D-200 Methyl Methyl H H

D-201 Methyl Methyl H H

D-202 Methyl Methyl H H

D-203 Methyl Methyl H H

D-204 Methyl Methyl H H

TABLE 18     R₁     R₂     R₃     R₄

D-205 Methyl Methyl H H

D-206 Methyl Methyl H H

D-207 Methyl Methyl H H

D-208 Methyl Methyl H H

D-209 Methyl Methyl H H

D-210 Methyl Methyl H H

D-211 Methyl Methyl H H

D-212 Methyl Methyl H H

D-213 Methyl Methyl H H

D-214 Methyl Methyl H H

D-215 Methyl Methyl H H

D-216 Methyl Methyl H H

TABLE 19     R₁     R₂     R₃     R₄

D-217 Methyl Methyl H H

D-218 Methyl Methyl H H

D-219 Methyl Methyl H H

D-220 Methyl Methyl H H

D-221 Methyl Methyl H H

D-222 Methyl Methyl H H

D-223 Methyl Methyl H H

D-224 Methyl Methyl H H

D-225 Methyl Methyl H H

D-226 Methyl Methyl H H

D-227 Methyl Methyl H H

D-228 Methyl Methyl H H

TABLE 20     R₁     R₂     R₃     R₄

D-229 Methyl Methyl H H

D-230 Methyl Methyl H H

D-231 Methyl Methyl H H

D-232 Methyl Methyl H H

D-233 Methyl Methyl H H

D-234 Methyl Methyl H H

D-235 Methyl Methyl H H

D-236 Methyl Methyl H H

D-237 Methyl Methyl H H

D-238 Methyl Methyl H H

D-239 Methyl Methyl H H

D-240 Methyl Methyl H H

TABLE 21     R₁     R₂     R₃     R₄

D-241 Methyl Methyl Methyl Methyl

D-242 Methyl Methyl Methyl Methyl

D-243 Methyl Methyl Methyl Methyl

D-244 Methyl Methyl Methyl Methyl

D-245 Methyl Methyl Methyl Methyl

D-246 Methyl Methyl Methyl Methyl

D-247 Methyl Methyl Methyl Methyl

D-248 Methyl Methyl Methyl Methyl

D-249 Methyl Methyl Methyl Methyl

D-250 Methyl Methyl Methyl Methyl

D-251 Methyl Methyl Methyl Methyl

D-252 Methyl Methyl Methyl Methyl

TABLE 22     R₁     R₂     R₃     R₄

D-253 Methyl Methyl Methyl Methyl

D-254 Methyl Methyl Methyl Methyl

D-255 Methyl Methyl Methyl Methyl

D-256 Methyl Methyl Methyl Methyl

D-257 Methyl Methyl Methyl Methyl

D-258 Methyl Methyl Methyl Methyl

D-259 Methyl Methyl Methyl Methyl

D-260 Methyl Methyl Methyl Methyl

D-261 Methyl Methyl Methyl Methyl

D-262 Methyl Methyl Methyl Methyl

D-263 Methyl Methyl Methyl Methyl

D-264 Methyl Methyl Methyl Methyl

TABLE 23     R₁     R₂     R₃     R₄

D-253 Methyl Methyl Methyl Methyl

D-254 Methyl Methyl Methyl Methyl

D-255 Methyl Methyl Methyl Methyl

D-256 Methyl Methyl Methyl Methyl

D-257 Methyl Methyl Methyl Methyl

D-258 Methyl Methyl Methyl Methyl

D-259 Methyl Methyl Methyl Methyl

D-260 Methyl Methyl Methyl Methyl

D-261 Methyl Methyl Methyl Methyl

D-262 Methyl Methyl Methyl Methyl

D-263 Methyl Methyl Methyl Methyl

D-264 Methyl Methyl Methyl Methyl

TABLE 24 R₁ R₂ R₃ R₄

D-277 Di-phenylAmino H H H

D-278 Di-phenylAmino H H H

D-279 Di-phenylAmino H H H

D-280 Di-phenylAmino H H H

D-281 Di-phenylAmino H H H

D-282 Di-phenylAmino H H H

D-283 Di-phenylAmino H H H

D-284 Di-phenylAmino H H H

D-285 Di-phenylAmino H H H

D-286 Di-phenylAmino H H H

D-287 Di-phenylAmino H H H

D-288 Di-phenylAmino H H H

TABLE 25 R₁ R₂ R₃ R₄

D-289 Methyl H Methyl H

D-290 Methyl H Methyl H

D-291 Methyl H Methyl H

D-292 Methyl H Methyl H

D-293 Methyl H Methyl H

D-294 Methyl H Methyl H

D-295 Methyl H Methyl H

D-296 Methyl H Methyl H

D-297 Methyl H Methyl H

D-298 Methyl H Methyl H

D-299 Methyl H Methyl H

D-300 Methyl H Methyl H

TABLE 26 R₁ R₂ R₃ R₄

D-301 Methyl H Methyl H

D-302 Methyl H Methyl H

D-303 Methyl H Methyl H

D-304 Methyl H Methyl H

D-305 Methyl H Methyl H

D-306 Methyl H Methyl H

D-307 Methyl H Methyl H

D-308 Methyl H Methyl H

D-309 Methyl H Methyl H

D-310 Methyl H Methyl H

D-311 Methyl H Methyl H

D-312 Methyl H Methyl H

TABLE 27     R₁     R₂     R₃     R₄

D-313 Methyl H Methyl H

D-314 Methyl H Methyl H

D-315 Methyl H Methyl H

D-316 Methyl H Methyl H

D-317 Methyl H Methyl H

D-318 Methyl H Methyl H

D-319 Methyl H Methyl H

D-320 Methyl H Methyl H

D-321 Methyl H Methyl H

D-322 Methyl H Methyl H

D-323 Methyl H Methyl H

D-324 Methyl H Methyl H

TABLE 28     R₁     R₂     R₃     R₄

D-325 Methyl H Methyl H

D-326 Methyl H Methyl H

D-327 Methyl H Methyl H

D-328 Methyl H Methyl H

D-329 Methyl H Methyl H

D-330 Methyl H Methyl H

D-331 Methyl H Methyl H

D-332 Methyl H Methyl H

D-333 Methyl H Methyl H

D-334 Methyl H Methyl H

D-335 Methyl H Methyl H

D-336 Methyl H Methyl H

TABLE 29 R₁ R₂ R₃ R₄

D-337 Iso-propyl H Iso-propyl H

D-338 Iso-propyl H Iso-propyl H

D-339 Iso-propyl H Iso-propyl H

D-340 Iso-propyl H Iso-propyl H

D-341 Iso-propyl H Iso-propyl H

D-342 Iso-propyl H Iso-propyl H

D-343 Iso-propyl H Iso-propyl H

D-344 Iso-propyl H Iso-propyl H

D-345 Iso-propyl H Iso-propyl H

D-346 Iso-propyl H Iso-propyl H

D-347 Iso-propyl H Iso-propyl H

D-348 Iso-propyl H Iso-propyl H

TABLE 30     R₁     R₂     R₃     R₄

D-349 Isopropyl H Isopropyl H

D-350 Isopropyl H Isopropyl H

D-351 Isopropyl H Isopropyl H

D-352 Isopropyl H Isopropyl H

D-353 Isopropyl H Isopropyl H

D-354 Isopropyl H Isopropyl H

D-355 Isopropyl H Isopropyl H

D-356 Isopropyl H Isopropyl H

D-357 Isopropyl H Isopropyl H

D-358 Isopropyl H Isopropyl H

D-359 Isopropyl H Isopropyl H

D-360 Isopropyl H Isopropyl H

TABLE 31     R₁     R₂     R₃     R₄

D-361 Isopropyl H Isopropyl H

D-362 Isopropyl H Isopropyl H

D-363 Isopropyl H Isopropyl H

D-364 Isopropyl H Isopropyl H

D-365 Isopropyl H Isopropyl H

D-366 Isopropyl H Isopropyl H

D-367 Isopropyl H Isopropyl H

D-368 Isopropyl H Isopropyl H

D-369 Isopropyl H Isopropyl H

D-370 Isopropyl H Isopropyl H

D-371 Isopropyl H Isopropyl H

D-372 Isopropyl H Isopropyl H

TABLE 32     R₁     R₂     R₃     R₄

D-373 Isopropyl H Isopropyl H

D-374 Isopropyl H Isopropyl H

D-375 Isopropyl H Isopropyl H

D-376 Isopropyl H Isopropyl H

D-377 Isopropyl H Isopropyl H

D-378 Isopropyl H Isopropyl H

D-379 Isopropyl H Isopropyl H

D-380 Isopropyl H Isopropyl H

D-381 Isopropyl H Isopropyl H

D-382 Isopropyl H Isopropyl H

D-383 Isopropyl H Isopropyl H

D-384 Isopropyl H Isopropyl H

TABLE 33 R₁ R₂ R₃ R₄

D-385 t-bu-tyl H t-bu-tyl H

D-386 t-bu-tyl H t-bu-tyl H

D-387 t-bu-tyl H t-bu-tyl H

D-388 t-bu-tyl H t-bu-tyl H

D-389 t-bu-tyl H t-bu-tyl H

D-390 t-bu-tyl H t-bu-tyl H

D-391 t-bu-tyl H t-bu-tyl H

D-392 t-bu-tyl H t-bu-tyl H

D-393 t-bu-tyl H t-bu-tyl H

D-394 t-bu-tyl H t-bu-tyl H

D-395 t-bu-tyl H t-bu-tyl H

D-396 t-bu-tyl H t-bu-tyl H

TABLE 34     R₁     R₂     R₃     R₄

D-397 t-butyl H t-butyl H

D-398 t-butyl H t-butyl H

D-399 t-butyl H t-butyl H

D-400 t-butyl H t-butyl H

D-401 t-butyl H t-butyl H

D-402 t-butyl H t-butyl H

D-403 t-butyl H t-butyl H

D-404 t-butyl H t-butyl H

D-404 t-butyl H t-butyl H

D-405 t-butyl H t-butyl H

D-406 t-butyl H t-butyl H

D-407 t-butyl H t-butyl H

D-408 t-butyl H t-butyl H

TABLE 35     R₁     R₂     R₃     R₄

D-409 t-butyl H t-butyl H

D-410 t-butyl H t-butyl H

D-411 t-butyl H t-butyl H

D-412 t-butyl H t-butyl H

D-413 t-butyl H t-butyl H

D-414 t-butyl H t-butyl H

D-415 t-butyl H t-butyl H

D-416 t-butyl H t-butyl H

D-417 t-butyl H t-butyl H

D-418 t-butyl H t-butyl H

D-419 t-butyl H t-butyl H

D-420 t-butyl H t-butyl H

TABLE 36     R₁     R₂     R₃     R₄

D-421 t-butyl H t-butyl H

D-422 t-butyl H t-butyl H

D-423 t-butyl H t-butyl H

D-424 t-butyl H t-butyl H

D-425 t-butyl H t-butyl H

D-426 t-butyl H t-butyl H

D-427 t-butyl H t-butyl H

D-428 t-butyl H t-butyl H

D-429 t-butyl H t-butyl H

D-430 t-butyl H t-butyl H

D-431 t-butyl H t-butyl H

D-432 t-butyl H t-butyl H

TABLE 37 R₁ R₂ R₃ R₄

D-433 Phe-nyl H Phe-nyl H

D-434 Phe-nyl H Phe-nyl H

D-435 Phe-nyl H Phe-nyl H

D-436 Phe-nyl H Phe-nyl H

D-437 Phe-nyl H Phe-nyl H

D-438 Phe-nyl H Phe-nyl H

D-439 Phe-nyl H Phe-nyl H

D-440 Phe-nyl H Phe-nyl H

D-441 Phe-nyl H Phe-nyl H

D-442 Phe-nyl H Phe-nyl H

D-443 Phe-nyl H Phe-nyl H

D-444 Phe-nyl H Phe-nyl H

TABLE 38     R₁     R₂     R₃     R₄

D-445 Phenyl H Phenyl H

D-446 Phenyl H Phenyl H

D-447 Phenyl H Phenyl H

D-448 Phenyl H Phenyl H

D-449 Phenyl H Phenyl H

D-450 Phenyl H Phenyl H

D-451 Phenyl H Phenyl H

D-452 Phenyl H Phenyl H

D-453 Phenyl H Phenyl H

D-454 Phenyl H Phenyl H

D-455 Phenyl H Phenyl H

D-456 Phenyl H Phenyl H

TABLE 39     R₁     R₂     R₃     R₄

D-457 Phenyl H Phenyl H

D-458 Phenyl H Phenyl H

D-459 Phenyl H Phenyl H

D-460 Phenyl H Phenyl H

D-461 Phenyl H Phenyl H

D-462 Phenyl H Phenyl H

D-463 Phenyl H Phenyl H

D-464 Phenyl H Phenyl H

D-465 Phenyl H Phenyl H

D-466 Phenyl H Phenyl H

D-467 Phenyl H Phenyl H

D-468 Phenyl H Phenyl H

TABLE 40     R₁     R₂     R₃     R₄

D-469 Phenyl H Phenyl H

D-470 Phenyl H Phenyl H

D-471 Phenyl H Phenyl H

D-472 Phenyl H Phenyl H

D-473 Phenyl H Phenyl H

D-474 Phenyl H Phenyl H

D-476 Phenyl H Phenyl H

D-477 Phenyl H Phenyl H

D-478 Phenyl H Phenyl H

D-479 Phenyl H Phenyl H

D-480 Phenyl H Phenyl H

TABLE 41 R₁ R₂ R₃ R₄

D-481 H Methyl H H

D-482 H Methyl H H

D-483 H Methyl H H

D-484 H Methyl H H

D-485 H Methyl H H

D-486 H Methyl H H

D-487 H Methyl H H

D-488 H Methyl H H

D-489 H Methyl H H

D-490 H Methyl H H

D-491 H Methyl H H

D-492 H Methyl H H

TABLE 42 R₁ R₂ R₃ R₄

D-493 H Methyl H H

D-494 H Methyl H H

D-495 H Methyl H H

D-496 H Methyl H H

D-497 H Methyl H H

D-498 H Methyl H H

D-499 H Methyl H H

D-500 H Methyl H H

D-501 H Methyl H H

D-502 H Methyl H H

D-503 H Methyl H H

D-504 H Methyl H H

TABLE 43 R₁ R₂ R₃ R₄

D-505 H Methyl H H

D-506 H Methyl H H

D-507 H Methyl H H

D-508 H Methyl H H

D-509 H Methyl H H

D-510 H Methyl H H

D-511 H Methyl H H

D-512 H Methyl H H

D-513 H Methyl H H

D-514 H Methyl H H

D-515 H Methyl H H

D-516 H Methyl H H

TABLE 44 R₁ R₂ R₃ R₄

D-517 H Methyl H H

D-518 H Methyl H H

D-519 H Methyl H H

D-520 H Methyl H H

D-521 H Methyl H H

D-522 H Methyl H H

D-523 H Methyl H H

D-524 H Methyl H H

D-525 H Methyl H H

D-526 H Methyl H H

D-527 H Methyl H H

D-528 H Methyl H H

TABLE 45 R₁ R₂ R₃ R₄

D-529 H Isopropyl H H

D-530 H Isopropyl H H

D-531 H Isopropyl H H

D-532 H Isopropyl H H

D-533 H Isopropyl H H

D-534 H Isopropyl H H

D-535 H Isopropyl H H

D-536 H Isopropyl H H

D-537 H Isopropyl H H

D-538 H Isopropyl H H

D-539 H Isopropyl H H

D-540 H Isopropyl H H

TABLE 46 R₁ R₂ R₃ R₄

D-541 H Isopropyl H H

D-542 H Isopropyl H H

D-543 H Isopropyl H H

D-544 H Isopropyl H H

D-545 H Isopropyl H H

D-546 H Isopropyl H H

D-547 H Isopropyl H H

D-548 H Isopropyl H H

D-549 H Isopropyl H H

D-550 H Isopropyl H H

D-551 H Isopropyl H H

D-552 H Isopropyl H H

TABLE 47 R₁ R₂ R₃ R₄

D-553 H Isopropyl H H

D-554 H Isopropyl H H

D-555 H Isopropyl H H

D-556 H Isopropyl H H

D-557 H Isopropyl H H

D-558 H Isopropyl H H

D-559 H Isopropyl H H

D-560 H Isopropyl H H

D-561 H Isopropyl H H

D-562 H Isopropyl H H

D-563 H Isopropyl H H

D-564 H Isopropyl H H

TABLE 48 R₁ R₂ R₃ R₄

D-565 H Isopropyl H H

D-566 H Isopropyl H H

D-567 H Isopropyl H H

D-568 H Isopropyl H H

D-569 H Isopropyl H H

D-570 H Isopropyl H H

D-571 H Isopropyl H H

D-572 H Isopropyl H H

D-573 H Isopropyl H H

D-574 H Isopropyl H H

D-575 H Isopropyl H H

D-576 H Isopropyl H H

TABLE 49 R₁ R₂ R₃ R₄

D-577 H t-butyl H H

D-578 H t-butyl H H

D-579 H t-butyl H H

D-580 H t-butyl H H

D-581 H t-butyl H H

D-582 H t-butyl H H

D-583 H t-butyl H H

D-584 H t-butyl H H

D-585 H t-butyl H H

D-586 H t-butyl H H

D-587 H t-butyl H H

D-588 H t-butyl H H

TABLE 50 R₁ R₂ R₃ R₄

D-589 H t-butyl H H

D-590 H t-butyl H H

D-591 H t-butyl H H

D-592 H t-butyl H H

D-593 H t-butyl H H

D-594 H t-butyl H H

D-595 H t-butyl H H

D-596 H t-butyl H H

D-597 H t-butyl H H

D-598 H t-butyl H H

D-599 H t-butyl H H

D-600 H t-butyl H H

TABLE 51 R₁ R₂ R₃ R₄

D-601 H t-butyl H H

D-602 H t-butyl H H

D-603 H t-butyl H H

D-604 H t-butyl H H

D-605 H t-butyl H H

D-606 H t-butyl H H

D-607 H t-butyl H H

D-608 H t-butyl H H

D-609 H t-butyl H H

D-610 H t-butyl H H

D-611 H t-butyl H H

D-612 H t-butyl H H

TABLE 52 R₁ R₂ R₃ R₄

D-613 H t-butyl H H

D-614 H t-butyl H H

D-615 H t-butyl H H

D-616 H t-butyl H H

D-617 H t-butyl H H

D-618 H t-butyl H H

D-619 H t-butyl H H

D-620 H t-butyl H H

D-621 H t-butyl H H

D-622 H t-butyl H H

D-623 H t-butyl H H

D-624 H t-butyl H H

TABLE 53 R₁ R₂ R₃ R₄

D-625 H Phenyl H H

D-626 H Phenyl H H

D-627 H Phenyl H H

D-628 H Phenyl H H

D-629 H Phenyl H H

D-630 H Phenyl H H

D-631 H Phenyl H H

D-632 H Phenyl H H

D-633 H Phenyl H H

D-634 H Phenyl H H

D-635 H Phenyl H H

D-636 H Phenyl H H

TABLE 54 R₁ R₂ R₃ R₄

D-637 H Phenyl H H

D-638 H Phenyl H H

D-639 H Phenyl H H

D-640 H Phenyl H H

D-641 H Phenyl H H

D-642 H Phenyl H H

D-643 H Phenyl H H

D-644 H Phenyl H H

D-645 H Phenyl H H

D-646 H Phenyl H H

D-647 H Phenyl H H

D-648 H Phenyl H H

TABLE 55 R₁ R₂ R₃ R₄

D-649 H Phenyl H H

D-650 H Phenyl H H

D-651 H Phenyl H H

D-652 H Phenyl H H

D-653 H Phenyl H H

D-654 H Phenyl H H

D-655 H Phenyl H H

D-656 H Phenyl H H

D-657 H Phenyl H H

D-658 H Phenyl H H

D-659 H Phenyl H H

D-660 H Phenyl H H

TABLE 56 R₁ R₂ R₃ R₄

D-661 H Phenyl H H

D-662 H Phenyl H H

D-663 H Phenyl H H

D-664 H Phenyl H H

D-665 H Phenyl H H

D-666 H Phenyl H H

D-667 H Phenyl H H

D-668 H Phenyl H H

D-669 H Phenyl H H

D-670 H Phenyl H H

D-671 H Phenyl H H

D-672 H Phenyl H H

TABLE 57 R₁ R₂ R₃ R₄

D-673 H Methyl H Methyl

D-674 H Methyl H Methyl

D-675 H Methyl H Methyl

D-676 H Methyl H Methyl

D-677 H Methyl H Methyl

D-678 H Methyl H Methyl

D-679 H Methyl H Methyl

D-680 H Methyl H Methyl

D-681 H Methyl H Methyl

D-682 H Methyl H Methyl

D-683 H Methyl H Methyl

D-684 H Methyl H Methyl

TABLE 58 R₁ R₂ R₃ R₄

D-685 H Methyl H Methyl

D-686 H Methyl H Methyl

D-687 H Methyl H Methyl

D-688 H Methyl H Methyl

D-689 H Methyl H Methyl

D-690 H Methyl H Methyl

D-691 H Methyl H Methyl

D-692 H Methyl H Methyl

D-693 H Methyl H Methyl

D-694 H Methyl H Methyl

D-695 H Methyl H Methyl

D-696 H Methyl H Methyl

TABLE 59 R₁ R₂ R₃ R₄

D-697 H Methyl H Methyl

D-698 H Methyl H Methyl

D-699 H Methyl H Methyl

D-700 H Methyl H Methyl

D-701 H Methyl H Methyl

D-702 H Methyl H Methyl

D-703 H Methyl H Methyl

D-704 H Methyl H Methyl

D-705 H Methyl H Methyl

D-706 H Methyl H Methyl

D-707 H Methyl H Methyl

D-708 H Methyl H Methyl

TABLE 60 R₁ R₂ R₃ R₄

D-709 H Methyl H Methyl

D-710 H Methyl H Methyl

D-711 H Methyl H Methyl

D-712 H Methyl H Methyl

D-713 H Methyl H Methyl

D-714 H Methyl H Methyl

D-715 H Methyl H Methyl

D-716 H Methyl H Methyl

D-717 H Methyl H Methyl

D-718 H Methyl H Methyl

D-719 H Methyl H Methyl

D-720 H Methyl H Methyl

TABLE 61 R₁ R₂ R₃ R₄

D-721 H Isopropyl H Isopropyl

D-722 H Isopropyl H Isopropyl

D-723 H Isopropyl H Isopropyl

D-724 H Isopropyl H Isopropyl

D-725 H Isopropyl H Isopropyl

D-726 H Isopropyl H Isopropyl

D-727 H Isopropyl H Isopropyl

D-728 H Isopropyl H Isopropyl

D-729 H Isopropyl H Isopropyl

D-730 H Isopropyl H Isopropyl

D-731 H Isopropyl H Isopropyl

D-732 H Isopropyl H Isopropyl

TABLE 62    R₁    R₂    R₃    R₄

D-733 H Isopropyl H Isopropyl

D-734 H Isopropyl H Isopropyl

D-735 H Isopropyl H Isopropyl

D-736 H Isopropyl H Isopropyl

D-737 H Isopropyl H Isopropyl

D-738 H Isopropyl H Isopropyl

D-739 H Isopropyl H Isopropyl

D-740 H Isopropyl H Isopropyl

D-741 H Isopropyl H Isopropyl

D-742 H Isopropyl H Isopropyl

D-743 H Isopropyl H Isopropyl

D-744 H Isopropyl H Isopropyl

TABLE 63    R₁    R₂    R₃    R₄

D-745 H Isopropyl H Isopropyl

D-746 H Isopropyl H Isopropyl

D-747 H Isopropyl H Isopropyl

D-748 H Isopropyl H Isopropyl

D-749 H Isopropyl H Isopropyl

D-750 H Isopropyl H Isopropyl

D-751 H Isopropyl H Isopropyl

D-752 H Isopropyl H Isopropyl

D-753 H Isopropyl H Isopropyl

D-754 H Isopropyl H Isopropyl

D-755 H Isopropyl H Isopropyl

D-756 H Isopropyl H Isopropyl

TABLE 64    R₁    R₂    R₃    R₄

D-757 H Isopropyl H Isopropyl

D-758 H Isopropyl H Isopropyl

D-759 H Isopropyl H Isopropyl

D-760 H Isopropyl H Isopropyl

D-761 H Isopropyl H Isopropyl

D-762 H Isopropyl H Isopropyl

D-763 H Isopropyl H Isopropyl

D-764 H Isopropyl H Isopropyl

D-765 H Isopropyl H Isopropyl

D-766 H Isopropyl H Isopropyl

D-767 H Isopropyl H Isopropyl

D-768 H Isopropyl H Isopropyl

TABLE 65    R₁    R₂    R₃    R₄

D-769 Cyclohexyl H H H

D-770 Cyclohexyl H H H

D-771 Cyclohexyl H H H

D-772 Cyclohexyl H H H

D-773 Cyclohexyl H H H

D-774 Cyclohexyl H H H

D-775 Cyclohexyl H H H

D-776 Cyclohexyl H H H

D-777 Cyclohexyl H H H

D-778 Cyclohexyl H H H

D-779 Cyclohexyl H H H

D-780 Cyclohexyl H H H

TABLE 66    R₁    R₂    R₃    R₄

D-781 Cyclohexyl H H H

D-782 Cyclohexyl H H H

D-783 Cyclohexyl H H H

D-784 Cyclohexyl H H H

D-785 Cyclohexyl H H H

D-786 Cyclohexyl H H H

D-787 Cyclohexyl H H H

D-788 Cyclohexyl H H H

D-789 Cyclohexyl H H H

D-790 Cyclohexyl H H H

D-791 Cyclohexyl H H H

D-792 Cyclohexyl H H H

TABLE 67    R₁    R₂    R₃    R₄

D-793 Cyclohexyl H Cyclohexyl H

D-794 Cyclohexyl H Cyclohexyl H

D-795 Cyclohexyl H Cyclohexyl H

D-796 Cyclohexyl H Cyclohexyl H

D-797 Cyclohexyl H Cyclohexyl H

D-798 Cyclohexyl H Cyclohexyl H

D-799 Cyclohexyl H Cyclohexyl H

D-800 Cyclohexyl H Cyclohexyl H

D-801 Cyclohexyl H Cyclohexyl H

D-802 Cyclohexyl H Cyclohexyl H

D-803 Cyclohexyl H Cyclohexyl H

D-804 Cyclohexyl H Cyclohexyl H

TABLE 68    R₁    R₂    R₃    R₄

D-805 Cyclohexyl H Cyclohexyl H

D-806 Cyclohexyl H Cyclohexyl H

D-807 Cyclohexyl H Cyclohexyl H

D-808 Cyclohexyl H Cyclohexyl H

D-809 Cyclohexyl H Cyclohexyl H

D-810 Cyclohexyl H Cyclohexyl H

D-811 Cyclohexyl H Cyclohexyl H

D-812 Cyclohexyl H Cyclohexyl H

D-813 Cyclohexyl H Cyclohexyl H

D-814 Cyclohexyl H Cyclohexyl H

D-815 Cyclohexyl H Cyclohexyl H

D-816 Cyclohexyl H Cyclohexyl H

TABLE 69    R₁    R₂    R₃    R₄

D-817 4-t-butylphemyl H H H

D-818 4-t-butylphemyl H H H

D-819 4-t-butylphemyl H H H

D-820 4-t-butylphemyl H H H

D-821 4-t-butylphemyl H H H

D-822 4-t-butylphemyl H H H

D-823 4-trimethylsilylphenyl H H H

D-824 4-trimethylsilylphenyl H H H

D-825 4-trimethylsilylphenyl H H H

D-826 4-trimethylsilylphenyl H H H

D-827 4-trimethylsilylphenyl H H H

D-828 4-trimethylsilylphenyl H H H

TABLE 70    R₁    R₂    R₃    R₄

D-829 4-cyanophenyl H H H

D-830 4-cyanophenyl H H H

D-831 4-cyanophenyl H H H

D-832 4-cyanophenyl H H H

D-833 4-cyanophenyl H H H

D-834 4-cyanophenyl H H H

D-835 4-trifluoromethylphenyl H H H

D-836 4-trifluoromethylphenyl H H H

D-837 4-trifluoromethylphenyl H H H

D-838 4-trifluoromethylphenyl H H H

D-839 4-trifluoromethylphenyl H H H

D-840 4-trifluoromethylphenyl H H H

TABLE 71    R₁    R₂    R₃    R₄

D-841 2-quinolyl H H H

D-842 2-quinolyl H H H

D-843 2-quinolyl H H H

D-844 2-quinolyl H H H

D-845 2-quinolyl H H H

D-846 2-quinolyl H H H

D-847 3-isoquinolyl H H H

D-848 3-isoquinolyl H H H

D-849 3-isoquinolyl H H H

D-850 3-isoquinolyl H H H

D-851 3-isoquinolyl H H H

D-852 3-isoquinolyl H H H

TABLE 72    R₁    R₂    R₃    R₄

D-853 1-adamanthyl H H H

D-854 1-adamanthyl H H H

D-855 1-pyrenyl H H H

D-856 1-pyrenyl H H H

D-857 1-pyrenyl H H H

D-858 1-pyrenyl H H H

D-859 1-pyrenyl H H H

D-860 1-pyrenyl H H H

D-861 1-pyrenyl H H H

D-862 1-pyrenyl H H H

D-863 1-pyrenyl H H H

D-864 1-pyrenyl H H H

TABLE 73    R₁    R₂    R₃    R₄

D-865 H Cyclohexyl H H

D-866 H Cyclohexyl H H

D-867 H Cyclohexyl H H

D-868 H Cyclohexyl H H

D-869 H Cyclohexyl H H

D-870 H Cyclohexyl H H

D-871 H Cyclohexyl H H

D-872 H Cyclohexyl H H

D-873 H Cyclohexyl H H

D-874 H Cyclohexyl H H

D-875 H Cyclohexyl H H

D-876 H Cyclohexyl H H

TABLE 74    R₁    R₂    R₃    R₄

D-877 H Cyclohexyl H H

D-878 H Cyclohexyl H H

D-879 H Cyclohexyl H H

D-880 H Cyclohexyl H H

D-881 H Cyclohexyl H H

D-882 H Cyclohexyl H H

D-883 H Cyclohexyl H H

D-884 H Cyclohexyl H H

D-885 H Cyclohexyl H H

D-886 H Cyclohexyl H H

D-887 H Cyclohexyl H H

D-888 H Cyclohexyl H H

TABLE 75    R₁    R₂    R₃    R₄

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

H Cyclohexyl H H

TABLE 76    R₁    R₂    R₃    R₄

D-901 H Cyclohexyl H H

D-902 H Cyclohexyl H H

D-903 H Cyclohexyl H H

D-904 H Cyclohexyl H H

D-905 H Cyclohexyl H H

D-906 H Cyclohexyl H H

D-907 H Cyclohexyl H H

D-908 H Cyclohexyl H H

D-909 H Cyclohexyl H H

D-910 H Cyclohexyl H H

D-911 H Cyclohexyl H H

D-912 H Cyclohexyl H H

TABLE 77    R₁    R₂    R₃    R₄

D-913 Methyl H Isopropyl H

D-914 Methyl H Isopropyl H

D-915 Methyl H Isopropyl H

D-916 Methyl H Isopropyl H

D-917 Methyl H Isopropyl H

D-918 Methyl H Isopropyl H

D-919 Methyl H Isopropyl H

D-920 Methyl H Isopropyl H

D-921 Methyl H Isopropyl H

D-922 Methyl H Isopropyl H

D-923 Methyl H Isopropyl H

D-924 Methyl H Isopropyl H

TABLE 78    R₁    R₂    R₃    R₄

D-925 Methyl H Isopropyl H

D-926 Methyl H Isopropyl H

D-927 Methyl H Isopropyl H

D-928 Methyl H Isopropyl H

D-929 Methyl H Isopropyl H

D-930 Methyl H Isopropyl H

D-931 Methyl H Isopropyl H

D-932 Methyl H Isopropyl H

D-933 Methyl H Isopropyl H

D-934 Methyl H Isopropyl H

D-935 Methyl H Isopropyl H

D-936 Methyl H Isopropyl H

TABLE 79    R₁    R₂    R₃    R₄

D-937 t-bytyl H Isopropyl H

D-938 t-bytyl H Isopropyl H

D-939 t-bytyl H Isopropyl H

D-940 t-bytyl H Isopropyl H

D-941 t-bytyl H Isopropyl H

D-942 t-bytyl H Isopropyl H

D-943 t-bytyl H Isopropyl H

D-944 t-bytyl H Isopropyl H

D-945 t-bytyl H Isopropyl H

D-946 t-bytyl H Isopropyl H

D-947 t-bytyl H Isopropyl H

D-948 t-bytyl H Isopropyl H

TABLE 80    R₁    R₂    R₃    R₄

D-949 t-bytyl H Isopropyl H

D-950 t-bytyl H Isopropyl H

D-951 t-bytyl H Isopropyl H

D-952 t-bytyl H Isopropyl H

D-953 t-bytyl H Isopropyl H

D-954 t-bytyl H Isopropyl H

D-955 t-bytyl H Isopropyl H

D-956 t-bytyl H Isopropyl H

D-957 t-bytyl H Isopropyl H

D-958 t-bytyl H Isopropyl H

D-959 t-bytyl H Isopropyl H

D-960 t-bytyl H Isopropyl H

TABLE 81 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-961 —H —H —H —H —Me —Me —Me —MeD-962 —H —H —H —H —Me

—Me

D-963 —H —H —H —H

D-964 —H —H —H —H

—Me

—Me D-965 —H —H —H —H

D-966 —Me —H —Me —H

D-967 —Me —Me —Me —Me

D-968

—H

—H —Me

—Me

D-969 —H —Me —H —Me

D970

—H

—H

TABLE 82 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-971 —H —H —H —H —Me

—Me

D-972 —H —H —H —H

D-973 —H —H —H —H —Me

—Me

D-974 —H —H —H —H

D-975 —H —H —H —H

D-976 —H —H —H —H

D-977 —H —H —H —H

D-978 —Me —H —Me —H —Me

—Me

D-979 —Me —Me —Me Me

D-980 —Me —H —Me —H

TABLE 83 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-981 —H —H —H —H —Me

—Me

D-982 —H —H —H —H

D-983 —H —H —H —H —Me

—Me

D-984 —H —H —H —H

D-985 —H —H —H —H

D-986 —H —H —H —H

D-987 —H —H —H —H

D-988 —Me —H —Me —H —Me

—Me

D-989 —H —H —H —H

D-990 —H —H —H —H

TABLE 84 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-991 —H —H —H —H

D-992 —H —H —H —H

D-993 —H —H —H —H

D-994 —H —H —H —H

D-995 —H —H —H —H

D-996 —H —H —H —H

D-997 —H —H —H —H

D-998 —H —H —H —H

D-999 —H —H —H —H

D-1000 —Me —H —H —H

TABLE 85 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-1001 —H —H —H —H

D-1002 —H —H —H —H

D-1003 —H —H —H —H

D-1004 —H —H —H —H

D-1005 —H —H —H —H

D-1006 —H —H —H —H

D-1007 —H —H —H —H

D-1008 —H —H —H —H

D-1009 —H —H —H —H

D-1010 —Me —H —Me —H

TABLE 86 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-1011 —H —H —H —H

D-1012 —H —H —H —H

D-1013 —H —H —H —H

D-1014 —H —H —H —H

D-1015 —H —H —H —H

D-1016 —H —H —H —H

D-1017 —H —H —H —H

D-1018 —H —H —H —H

D-1019 —H —H —H —H

D-1020 —Me —H —Me —H

TABLE 87 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-1021 —H —H —H —H

D-1022 —H —H —H —H

D-1023 —H —H —H —H

D-1024 —H —H —H —H

D-1025 —H —H —H —H

D-1026 —H —H —H —H

D-1027 —H —H —H —H

D-1028 Me —H Me —H

D-1029 —H —H —H —H

D-1030 —H —H —H —H

TABLE 88 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-1031 —H —H —H —H

D-1032 —H —H —H —H

D-1033 —H —H —H —H

D-1034 —H —H —H —H

D-1035 —H —H —H —H

D-1036 —H —H —H —H

D-1037 —H —H —H —H

D-1038 —H —H —H —H

D-1039 —H —H —H —H

D-1040 —Me —H —Me —H

TABLE 89 No R₅ R₆ R₇ R₈ A₅ A₆ A₇ A₈ D-1041 —H —H —H —H

D-1042 —H —H —H —H

D-1043 —H —H —H —H

D-1044 —H —H —H —H

D-1045 —H —H —H —H

D-1046 —H —H —H —H

D-1047 —H —H —H —H

D-1048 Me —H Me —H

D-1049 —H —H —H —H

D-1050 —H —H —H —H

In the aromatic amine derivative of the present invention, since thearyl group (in particular, a benzene ring), the alkyl group, thecycroalkyl group or the heterocyclic group is connected to adiaminocrysene structure as a light emission center, an associationbetween the compounds is prevented, resulting in a prolonged lifetimethereof. Moreover, because coupling a bulky substituent to the chrysenebackbone structure increases a steric repulsion against the aminestructure, the lifetime prolongs further.

Further, the aromatic amine derivatives have a strong fluorescence in asolid state, and are excellent in an electric field light emission,which leads to a fluorescent quantum efficiency as high as 0.3 or more.In addition, the aromatic amine derivatives of the present inventionexhibit not only excellent capabilities of injecting and transportingholes from the metal electrode or organic thin film layers, but alsoexcellent capabilities of injecting and transporting electrons from themetal electrode or organic thin film layers and, therefore, are usefullyemployable as light emitting materials, particularly doping materialsfor organic EL devices. Besides, the aromatic amine derivatives of thepresent invention may be used together with other hole transportingmaterials, electron transporting materials or doping materials.

The organic EL device of the present invention comprises one or pluralorganic thin film layers sandwiched between an anode and a cathode. Inthe case of one layer type, a light emitting layer as the organic thinfilm layer is sandwiched between the anode and cathode. The lightemitting layer contains the light emitting material and may furthercontain a hole injecting material and an electron injecting material inorder to transport holes injected from the anode or electrons injectedfrom the cathode to the light emitting material. The aromatic aminederivatives of the present invention have an enhanced light emittingproperty and excellent hole injecting capability and hole transportingcapability as well as excellent electron injecting capability andelectron transporting capability and, therefore, can be employed as alight emitting material or a doping material in the light emittinglayer.

In the organic EL device of the present invention, the light emittinglayer contains the aromatic amine derivative of the present invention inan amount of preferably 0.1 to 20% by weight and more preferably 1 to10% by weight. Further, the aromatic amine derivatives of the presentinvention exhibit not only an extremely high fluorescent quantumefficiency but also high hole transporting capability and electrontransporting capability, and further are capable of forming a uniformthin film, so that the light emitting layer may be formed from thearomatic amine derivatives only.

On the other hand, in the case where the organic EL device of thepresent invention comprises two or more organic thin film layers havingat least the light emitting layer which are sandwiched between thecathode and anode, the organic thin film layers preferably include anorganic layer containing the aromatic amine derivative of the presentinvention as an essential component which is provided between the anodeand the light emitting layer. Such an organic layer may be a holeinjecting layer, a hole transporting layer, etc.

Further, in a case where the aromatic amine derivative of the presentinvention is employed as a doping material, it is preferable that atleast one kind selected from the group consisting of anthracenederivatives of a following general formula (3), anthracene derivativesof a following general formula (4) and pyrene derivatives of a followinggeneral formula (5) is employed as a host material.

In the general formula (3), X₁ and X₂ each independently represents ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted aryl group having 5 to 50ring carbon atoms, a substituted or unsubstituted aralkyl group having 6to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxylgroup having 1 to 50 ring carbon atoms, a substituted or unsubstitutedaryloxy group having 5 to 50 ring carbon atoms, a substituted orunsubstituted arylamino group having 5 to 50 ring carbon atoms, asubstituted or unsubstituted alkylamino group having 1 to 20 carbonatoms, a substituted or unsubstituted heterocyclic group having 5 to 50ring carbon atoms or a halogen atom; e and f each independentlyrepresents an integer of 0 to 4; when e or f is 2 or greater, X₁ and X₂may be the same with or different from each other.

Ar₁ and Ar₂ each independently represents a substituted or unsubstitutedaryl group having 5 to 50 ring carbon atoms or a substituted orunsubstituted heterocyclic group having 5 to 50 ring carbon atoms; atleast one of Ar₁ or Ar₂ represents a substituted or unsubstituted arylgroup with a condensed ring and having 10 to 50 ring carbon atoms; and mrepresents an integer of 1 to 3. When m is 2 or greater, a group withinthe above parentheses: [ ] may be the same with or different from eachother.

Specific examples and substituents of the X₁, X₂, Ar₁ and Ar₂ are thesame as those explained about the foregoing general formula (1).

In the general formula (4), X₁ to X₃ each independently represents ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted aryl group having 5 to 50ring carbon atoms, a substituted or unsubstituted aralkyl group having 6to 50 ring carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxylgroup having 1 to 50 carbon atoms, a substituted or unsubstitutedaryloxy group having 5 to 50 ring carbon atoms, a substituted orunsubstituted arylamino group having 5 to 50 ring carbon atoms, asubstituted or unsubstituted alkylamino group having 1 to 20 carbonatoms, a substituted or unsubstituted heterocyclic group having 5 to 50ring carbon atoms or a halogen atom; e, f, and g each independentlyrepresents an integer of 0 to 4. When e, f, or g is 2 or greater, X₁, X₂and X₃ may be the same with or different from each other.

Ar₁ represents a substituted or unsubstituted aryl group with acondensed ring and having 10 to 50 ring carbon atoms and Ar³ representsa substituted or unsubstituted aryl group having 5 to 50 ring carbonatoms; n represents an integer of 1 to 3. When n is 2 or greater, agroup within the above parentheses: [ ] may be the same with ordifferent from each other.

Specific examples and substituents of the X₁ to X₃, Ar₁ and Ar₃ are thesame as those explained about the foregoing general formula (1).

Specific examples of anthracene derivative represented by the generalformulae (3) and (4) will be illustrated below, though not particularlylimited thereto.

In the general formula (5), Ar₅ and Ar₆ each represents a substituted orunsubstituted aryl group having 6 to 50 ring carbon atoms;

-   L₁ and L₂ each independently represents a substituted or    unsubstituted phenylene group, a substituted or unsubstituted    naphthalenylene group, a substituted or unsubstituted fluorenylene    group or a substituted or unsubstituted dibenzosilolylene group;-   s represents an integer of 0 to 2, p represents an integer of 1 to    4, q represents an integer of 0 to 2 and r represents an integer of    0 to 4; and-   L₁ or Ar₅ bonds to any one of 1 to 5 position of pyrene, also L₂ or    Ar₆ bonds to any one of 6 to 10 position thereof,-   however, when p+r is an even number, Ar₅, Ar₆, L₁ and L₂ satisfy a    following requirement (1) or a requirement (2):-   (1) Ar₅≠Ar₆ and/or L₁≠L₂ (wherein ≠means that each group has a    different structure)-   (2) when Ar₅=Ar₆ and L₁=L₂-   (2-1) s≠q and/or p≠r, or-   (2-2) when s=q, and p=r,-   (2-2-1) both L₁ and L₂ or pyrene each bond respectively to different    positions of Ar₅ and Ar₆, or-   (2-2-2) both L₁ and L₂ or pyrene each bonds respectively to the same    position of Ar₅ and Ar₆, excluding a case where both L₁ and L₂ or    both Ar₅ and Ar₆ bond to 1 and 6 positions thereof, or 2 and 7    positions thereof.

Specific examples and substituents of the Ar₅, Ar₆, L₁ and L₂ are thesame as those explained about the foregoing general formula (1).

Specific examples of the pyrene derivative represented by the generalformula (5) will be illustrated below, though not particularly limitedthereto.

Examples of the organic EL device of a multilayer type include thosehaving multilayer structures such as (an anode/a hole injecting layer/alight emitting layer/a cathode), (an anode/a light emitting layer/anelectron injecting layer/a cathode) and (an anode/a hole injectinglayer/a light emitting layer/an electron injecting layer/a cathode).

The multilayers may also optionally contain, in addition to the aromaticamine derivatives of the present invention, conventionally knownmaterials such as light emitting materials, doping materials, holeinjecting materials and electron injecting materials according torequirements. The organic EL device having such a multilayer structurecan be prevented from suffering from deterioration in luminance andlifetime due to quenching. If required, the light emitting materials,doping materials, hole injecting materials and electron injectingmaterials may be used in combination with each other. The use of thedoping materials enables the resultant device to be improved inluminance of light emission and efficiency of light emission, andfurther emit a red color light or a blue color light. Further, in theorganic EL device of the present invention, the hole injecting layer,the light emitting layer and the electron injecting layer mayrespectively have a multilayer structure including two or more layers.In these cases, a layer injecting holes from the electrode is called asa hole injecting layer, and a layer for accepting the holes from thehole injecting layer and transporting the holes to the light emittinglayer is called as a hole transporting layer. Also, a layer injectingelectrons the electrode is called as an electron injecting layer, and alayer transporting for accepting the electrons from the electroninjecting layer and transporting the electrons to the light emittinglayer is called as an electron transporting layer. Those respectivelayers may be selectively used according to various factors such asenergy level of the materials used, heat resistance, and adhesion to theorganic thin film layers or the metal electrodes.

Examples of the host material or the doping material besides theforegoing general formulae (3) to (5) employable for the light emittinglayer together with the aromatic amine derivative of the presentinvention include condensed mass aromatic compound such as naphthalene,phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene,chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spiro fluorene, 9,10-diphenylanthracene,9,10-bis(phenyl-ethynyl)anthracene, 1,4-bis(9′-ethynylanthracenyl)benzene and those derivatives; organometallic complex suchas tris(8-quinolinolat)aluminium,bis-(2-methyl-8-quinolinolat)-4-(phenylphenolinat)aluminum, etc.;triarylamine derivative, styryl amine derivative, stilbene derivative,coumarine derivative, pyran derivative, oxazone derivative,benzothiazole derivative, benzoxazole derivative, benzimidazolederivative, pyrazine derivative, cinnamate ester derivative, diketopyrrolopyrrole derivative, acridone derivative, quinacridon derivative,etc.; though not particularly limited thereto.

The hole injecting material is preferably made of compounds which have agood hole transporting capability as well as excellent capabilities ofaccepting holes injected from the anode and injecting the holes into thelight emitting layer or light emitting material, prevent excitedparticles produced in the light emitting layer from moving into theelectron injecting layer or electron injecting material, and exhibit anexcellent capability of forming a thin film. Specific examples of thehole injecting material include phthalocyanine derivatives,naphthalocyanine derivatives, porphyrin derivatives, oxazole,oxadiazole, triazole, imidazole, imidazolone, imidazole thione,pyrazoline, pyrazolone, tetrahydroimidazole, hydrazone, acyl hydrazone,polyaryl alkanes, stilbene, butadiene, benzidine-type triphenyl amine,styryl amine-type triphenyl amine, diamine-type triphenyl amine andderivatives thereof, as well as polyvinyl carbazoles, polysilanes, andhigh molecular materials such as electro-conductive polymers, though notparticularly limited thereto.

Among those hole injecting materials usable in the organic EL device ofthe present invention, more effective hole injecting materials arearomatic tertiary amine derivatives and phthalocyanine derivatives.

Specific examples of the aromatic tertiary amine derivatives includetriphenyl amine, tritolyl amine, tolyldiphenyl amine,N,N′-diphenyl-N,N′-(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine,N,N,N′,N′-(4-methylphenyl)-1,1′-phenyl-4,4′-diamine,N,N,N′,N′-(4-methylphenyl)-1,1′-biphenyl-4,4′-diamine,N,N′-diphenyl-N,N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine,N,N′-(methylphenyl)-N,N′-(4-n-butylphenyl)-phenanthrene-9,10-diamine,N,N-bis(4-di-4-tolylaminophenyl)-4-phenyl-cylcohexane, and oligomers andpolymers having these aromatic tertiary amine skeletons, though notparticularly limited thereto.

Specific examples of the phthalocyanine (Pc) derivatives includephthalocyanine derivatives such as H₂Pc, CuPc, CoPc, NiPc, ZnPc, PdPc,FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl₂SiPc, (HO)AlPc, (HO)GaPc,VOPc, TiOPc, MoOPc, GaPc-O—GaPc, as well as naphthalocyaninederivatives, though not particularly limited thereto.

Also, in the organic EL device of the present invention, between thelight emitting layer and the anode, there is preferably formed a layersuch as the above hole transporting layer or hole injecting layercontaining those aromatic tertiary amine derivatives and/orphthalocyanine derivatives,.

The electron injecting material is preferably made of compounds whichhave a good electron transporting capability as well as excellentcapabilities of accepting electrons injected from the cathode andinjecting the electrons into the light emitting layer or light emittingmaterial, prevent excited particles produced in the light emitting layerfrom moving into the hole injecting layer, and exhibit an excellentcapability of forming a thin film. Specific examples of the electroninjecting material include fluorenone, anthraquinodimethane,diphenoquinone, thiopyrane dioxide, oxazole, oxadiazole, triazole,imidazole, perylenetetracarboxylic acid, fluorenylidene methane,anthrone, and derivatives thereof, though not particularly limitedthereto. Further, an electron accepting substance and an electrondonating substance may be added to the hole injecting material and theelectron injecting material, respectively, for enhanced sensitizationthereof.

In the organic EL device of the present invention, among these electroninjecting materials, more effective electron injecting materials aremetal complex compounds and five-member ring derivatives having anitrogen atom.

Specific examples of the metal complex compounds include8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc,bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese,tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)beryllium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato)gallium,bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, andbis(2-methyl-8-quinolinato)(2-naphtholato)gallium, though notparticularly limited thereto.

The five-member ring derivatives having a nitrogen atom are preferablyderivatives of oxazole, thiazole, oxadiazole, thiadiazole or triazole.Specific examples of the nitrogen-containing five-member ringderivatives include 2,5-bis(1-phenyl)-1,3,4-oxazole, dimethyl POPOP,2,5-bis(1-phenyl)-1,3,4-thiazole, 2,5-bis(1-phenyl)-1,3,4-oxadiazole,2-(4′-tert-butylphenyl)-5-(4″-biphenyl)-1,3,4-oxadiazole,2,5-bis(1-naphthyl)-1,3,4-oxadiazole,1,4-bis[2-(5-phenyloxadiazolyl)]benzene,1,4-bis[2-(5-phenyloxadiazolyl)-4-tert-butylbenzene],2-(4′-tert-butylphenyl)-5-(4″-biphenyl)-1,3,4-thiadiazole,2,5-bis(1-naphthyl)-1,3,4-thiadiazole,1,4-bis[2-(5-phenylthiadiazolyl)]benzene,2-(4′-tert-butylphenyl)-5-(4″-biphenyl)-1,3,4-triazole,2,5-bis(1-naphthyl)-1,3,4-triazole, and1,4-bis[2-(5-phenyltriazolyl)]benzene, though not particularly limitedthereto.

In the organic EL device of the present invention, the light emittinglayer may also optionally contain, in addition to the aromatic aminederivatives represented by the general formula (1), at least onematerial selected from the group consisting of light emitting materials,doping materials, hole injecting materials and electron injectingmaterials. The organic EL device of the present invention may be furtherprovided with a protective layer on a surface thereof, or the whole partthereof may be protected with silicone oil, resins, etc., in order toenhance stability thereof against temperature, humidity, atmosphere,etc.

The anode of the organic EL device according to the present inventionmay be suitably made of an electro-conductive material having a workfunction more than 4 eV. Examples of the electro-conductive material forthe anode include carbon, aluminum, vanadium, iron, cobalt, nickel,tungsten, silver, gold, platinum, palladium and alloys thereof, metaloxides such as tin oxide and indium oxide which are used for ITOsubstrates or NESA substrates, and organic electro-conductive resinssuch as polythiophene and polypyrrole. The cathode of the organic ELdevice according to the present invention may be suitably made of anelectro-conductive material having a work function of 4 eV or less.Examples of the electro-conductive material for the cathode includemagnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium,manganese, aluminum, lithium fluoride and alloys thereof, though notparticularly limited thereto. Typical examples of the alloys includealloys of magnesium and silver, alloys of magnesium and indium, andalloys of lithium and aluminum, though not particularly limited thereto.The ratio between the constituting metals in the alloys may becontrolled and appropriately determined depending upon temperature ofvapor deposition sources, atmosphere, vacuum degree, etc. The anode andcathode may be constituted of two or more layers, if required.

At least one surface of the organic EL device of the present inventionpreferably exhibits a sufficient transparency in a wavelength range oflight emitted therefrom in order to enhance an efficiency of lightemission thereof. Further, the substrate for the device is alsopreferably transparent. The transparent electrode is formed using theabove electro-conductive material by vapor deposition method, sputteringmethod, etc., so as to ensure a desirable transparency thereof. Theelectrode disposed on a light emitting surface of the device preferablyhas a light transmittance of 10% or greater. The substrate is notparticularly limited as long as it suitably has a good mechanical andthermal strength as well as a good transparency. Examples of thesubstrate include glass substrates and transparent resin films. Specificexamples of the transparent resin films include films made ofpolyethylene, ethylene-vinyl acetate copolymer, ethylene-vinyl alcoholcopolymer, polypropylene, polystyrene, polymethyl methacrylate,polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylons,polyether ether ketones, polysulfones, polyether sulfones,tetrafluoroethylene-perfluoroalkylvinyl ether copolymer, polyvinylfluoride, tetrafluoroethylene-ethylene copolymer,tetrafluororethylene-hexafluoropropylene copolymer,polychlorotrifluoroethylene, polyvinylidene fluoride, polyesters,polycarbonates, polyurethanes, polyimides, polyether imides andpolypropylene.

The respective layers of the organic EL device of the present inventionmay be formed by either a dry film-forming process such as vacuumdeposition, sputtering, plasma and ion-plating, or a wet film-formingprocess such as spin-coating, dipping and flow-coating. The thickness ofthe respective layers is not particularly limited, but should beadjusted to an appropriate range. When the thickness is too large, alarge electric voltage must be applied to the device in order to achievea predetermined light output, resulting in a poor efficiency of lightemission. On the other hand, when the thickness is too small, pinholestend to be formed in the layers, thereby failing to obtain a sufficientluminance of light emission even upon applying an electric fieldthereto. The suitable thickness of the respective layers is usually inthe range of from 5 nm to 10 μm and preferably from 10 nm to 0.2 μm.

In the wet film-forming process, materials constituting the respectivelayers are dissolved or dispersed in a suitable solvent such as ethanol,chloroform, tetrahydrofuran and dioxane to form a thin film thereof Thesolvent used for forming the respective layers is not particularlylimited. Also, suitable resins or additives may be added to therespective organic thin film layers for the purposes of improving afilm-forming property, preventing formation of pinholes in the resultantfilm, etc. Examples of the resins usable for the above purposes includeinsulating resins such as polystyrene, polycarbonates, polyarylates,polyesters, polyamides, polyurethanes, polysulfones, polymethylmethacrylate, polymethyl acrylate and celluloses as well as copolymersthereof, photoconductive resins such as poly-N-vinyl carbazole andpolysilanes, and electro-conductive resins such as polythiophene andpolypyrrole. Examples of the additives include antioxidants, ultravioletabsorbers and plasticizers.

The organic EL device of the present invention is suitably applied to,for example, planar light-emitting members such as a wall-hanging typetelevision flat panel displays or so, light sources for copiers,printers, back light for liquid crystal displays and, measuringinstruments, display panels, marker light, etc. Further, the material ofthe present invention can be used not only for organic EL devices butalso in other applications such as electronic photographic members,photoelectric converter elements, solar cells, image sensors, etc.

EXAMPLE

The present invention will be described in more detail by reference tothe following examples.

Synthesis Example 1 Synthesis of Chemical Compound (4)

(1-1) Synthesis of 2-bromo-6-methylnaphthalene

Under an atmospheric argon gas flow, trifluoromethane sulfonicacid-6-bromo-2-naphthyl ester in an amount of 32 g (90 mmol),dichloro(diphenylphosphinoferrocene)palladium in an amount of 3.6 g (5%by mol), lithium bromide in an amount of 7.8 g (90 mmol) and desiccatedtetrahydrofuran in an amount of 100 milliliter were placed into a threeneck flask with cooling pipe and having a capacity of 500 milliliter,and then, the resultant solution was cooled down to −20° C. After slowlydripping methylmagnesiumbromide in an amount of 90 milliliter (90 mmol,1 mol/liter (tetrahydrofuran)) into the flask, the resultant solutionwas stirred under heating at the temperature of 80° C. for 4 hours.After the reaction terminated, adding dilute hydrochloric acid in anamount of 100 milliliter into the reacted solution, an organic layer wasseparated and washed with the use of sodium bicarbonate solution andsodium chloride solution, followed by drying with the use of magnesiumsulfate. After removing the solvent by distillation by means of a rotaryevaporator, the resultant crude product was refined by means of columnchromatography (silicagel, hexane/dichloromethane=90/10), and as aresult, 9.4 g of aimed compound (white crystal) was obtained (yield:47%).

(1-2) Synthesis of 2-(6-methyl-2-naphthyl)benzaldehyde

Under an atmospheric argon gas flow, 2-bromo-6-methylnaphthalene in anamount of 6.6 g (30 mmol), 2-formylphenylboronic acid in an amount of5.4 g (36 mmol), (tetrakistriphenylphosphine)palladium in an amount of0.7 g (0.6 mmol), 2N sodium carbonate aqueous solution in an amount of45 milliliter and dimethoxyethane in an amount of 90 milliliter wereplaced into a three neck flask with a cooling pipe and having a capacityof 500 milliliter, and the resultant solution was refluxed under heatingfor 8 hours. After the reaction terminated, adding water in an amount of100 milliliter into the reacted solution, an organic layer was separatedand washed with the use of sodium chloride solution, followed by dryingwith the use of magnesium sulfate. After removing the solvent bydistillation by means of a rotary evaporator, the resultant crudeproduct was refined by means of column chromatography (silicagel,hexane/dichloromethane=60/40), and as a result, 6.7 g of aimed compound(white crystal) was obtained (yield: 91%).

(1-3) Synthesis of 2-((2-methoxyvinyl)phenyl)-6-methylnaphthalene

Under an atmospheric argon gas flow, 2-(6-methyl-2-naphthyl)benzaldehydein an amount of 13.7 g (55 mmol),(methoxymethyl)triphenylphosphoniumchloride in an amount of 21 g (61mmol), t butoxy potassium in an amount of 7.5 g (67 mmol) and desiccatedtetrahydrofuran in an amount of 250 milliliter were placed into a threeneck flask with a cooling pipe and having a capacity of 500 milliliter,and the resultant solution was stirred at the room temperature for anight. After the reaction terminated, adding water in an amount of 100milliliter into the reacted solution, an organic layer was separated,followed by drying with the use of magnesium sulfate. After removing thesolvent by distillation by means of a rotary evaporator, the resultantcrude product was refined by means of column chromatography (silicagel,hexane/dichloromethane=10/90), and as a result, 12.8 g of aimed compound(white crystal) was obtained (yield: 84%).

(1-4) Synthesis of 2-methylchrysene

Under an atmospheric argon gas flow,2-((2-methoxyvinyl)phenyl)-6-methylnaphthalene in an amount of 12.8 g(46 mmol), several drops of methyl acid, and desiccated dichloromethanein an amount of 100 milliliter were placed into a three necked-flaskequipped with a cooling pipe and having a capacity of 500 milliliter,and the resultant solution was stirred at the room temperature for 8hours. After the reaction terminated, adding sodium bicarbonate solutionin an amount of 100 milliliter into the reacted solution, crystals wereseparated by filtration. The resultant crude product was washed with theuse of water and methanol, and then, it was vacuum dried at thetemperature of 50° C. for 8 hours, and as a result, 8.2 g of aimedcompound (white crystal) was obtained (yield: 73%).

(1-5) Synthesis of 2-methyl-6,12-dibromochrysene

Under an atmospheric argon gas flow, 2-methylchrysene in an amount of8.2 g (34 mmol), N-bromosuccinimide in an amount of 14.5 g (81 mmol) andN,N-dimethylformamide in an amount of 400 milliliter were placed into athree neck flask with a cooling pipe and having a capacity of 1 liter,and the resultant solution was stirred at the room temperature for onenight. After the reaction terminated, adding water in an amount of 300milliliter into the reacted solution, crystals were separated byfiltration. The resultant crude product was washed with the use of waterand methanol, and then, it was re-crystallized in 100 milliliter oftoluene, and as a result, 8.8 g of aimed compound (white crystal) wasobtained (yield: 65%).

(1-6) Synthesis of Chemical Compound (4)

Under an atmospheric argon gas flow, 2-methyl-6,12-dibromochrysene in anamount of 4.0 g (10 mmol), bis(3,4-dimethylphenyl)amine in an amount of5.6 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% by mol),tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliterwere placed into a three-necked flask equipped with a cooling pipe andhaving a capacity of 300 milliliter, and the resultant solution wasstirred under heating at a temperature of 100° C. for one night. Afterthe reaction terminated, precipitated crystals were separated byfiltration and washed with the use of 50 milliliter of toluene and 100milliliter of methanol, and as a result, 5.8 g of pale yellow powderswere obtained. The pale yellow powders were identified as Compound (4)from the result in accordance with Field Desorption Mass Spectrum(FD-MS) measurement (yield: 85%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (4) is shown inFIG. 1. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (4) among the toluene solvent were400 nm and 456 nm respectively.

Synthesis Example 2 Synthesis of Compound (9)

(2-1) Synthesis of 2-isopropyl-6,12-dibromochrysene

An aimed compound was obtained in a similar manner as Synthesis Example1 from the step (1-1) to the step (1-5) except that isopropylmagnesiumbromide was employed instead of methylmagnesium bromide in the step(1-1).

(2-2) Synthesis of Compound (9)

Under an atmospheric argon gas flow, 2-isopropyl-6,12-dibromochrysene inan amount of 4.2 g (10 mmol), 4-isopropylphenyl-p-tolyl amine in anamount of 5.6 g (25 mmol), palladium acetate in an amount of 0.03 g(1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodiumin an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of100 milliliter were placed into a three-necked flask equipped with acooling pipe and having a capacity of 300 milliliter, and the resultantsolution was stirred under heating at a temperature of 100° C. for onenight. After the reaction terminated, precipitated crystals wereseparated by filtration and washed with the use of 50 milliliter oftoluene and 100 milliliter of methanol, and as a result, 6.4 g of paleyellow powders were obtained. The obtained product was identified to beCompound (9) in accordance with FD-MS measurement (yield: 90%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (9) is shown inFIG. 2. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (9) among the toluene solvent were407 nm and 453 nm respectively.

Synthesis Example 3 Synthesis of Chemical Compound (20)

(3-1) Synthesis of 2-bromo-6-isopropylnaphthalene

Under an atmospheric argon gas flow, trifluoromethane sulfonicacid-6-bromo-2-naphthyl ester in an amount of 32 g (90 mmol),dichloro(diphenylphosphinoferrocene)palladium in an amount of 3.6 g (5%by mol), lithium bromide in an amount of 7.8 g (90 mmol) and desiccatedtetrahydrofuran in an amount of 100 milliliter were placed into threenecked-flask equipped with cooling pipe and having a capacity of 500milliliter, and then, the resultant solution was cooled down to −20° C.After slowly dripping isopropylmagnesiumbromide in an amount of 90milliliter (90 mmol, 1 mol/liter (tetrahydrofuran)) into the flask, theresultant solution was stirred under heating at the temperature of 80°C. for 4 hours. After the reaction terminated, adding dilutehydrochloric acid in an amount of 100 milliliter into the reactedsolution, an organic layer was separated and washed with the use ofsodium bicarbonate solution and sodium chloride solution, followed bydrying with the use of magnesium sulfate. After removing the solvent bydistillation by means of a rotary evaporator, the resultant crudeproduct was refined by means of column chromatography (silicagel,hexane/dichloromethane=90/10), and as a result, 9.4 g of aimed compound(white crystal) was obtained (yield: 33%).

(3-2) Synthesis of 6-isopropylnaphthalene-2-boronic acid

Under an atmospheric argon gas flow, 2-bromo-6-isopropylnaphthalene inan amount of 9.4 g (38 mmol), desiccated ether in an amount of 100milliliter and desiccated toluen in an amount of 50 milliliter wereplaced into a three necked-flask equipped with cooling pipe and having acapacity of 500 milliliter, and then, the resultant solution was cooleddown to −40° C. After slowly dripping n-butyllithium in an amount of 25milliliter (40 mmol, 1.58M (n-hexane)) into the flask, the resultantsolution was stirred at a temperature of −20° C. for 2 hours.Subsequently, the solution was cooled down to −40° C. and then, slowlydripping boronic acid triisopropylester in an amount of 26 milliliter(114 mmol), the resultant solution was stirred at the room temperaturefor one night. After the reaction terminated, adding dilute hydrochloricacid in an amount of 100 milliliter into the reacted solution, anorganic layer was separated and washed with the use of sodium chloridesolution, followed by drying with the use of magnesium sulfate. Afterremoving the solvent by distillation by means of a rotary evaporator,the resultant crude product was washed with the use of 100 milliliter oftoluene and as a result, 5.0 g of an aimed compound (white crystal) wasobtained (yield: 63%).

(3-3) Synthesis of 5-isopropyl-2-(6-isopropyl-2-naphthyl)benzaldehyde

Under an atmospheric argon gas flow, 2-hydroxy-5-isopropylbenzaldehydein an amount of 4.4 g (27 mmol), trifluoromethane sulfonic acidanhydride in an amount of 11.2 g (40 mmol), pyridine in an amount of 6milliliter (80 mmol) and dichloromethane in an amount of 100 milliliterwere placed into a three necked-flask equipped with a cooling pipe andhaving a capacity of 500 milliliter, and the resultant solution wasstirred at the room temperature for 2 hours. After the reactionterminated, the resultant was separated by filtration, and after washingthe resultant crude product with the use of hexane and dichloromethane,the resultant solution was vacuum dried at a temperature of 50° C. for 8hours and as a result, 6.0 g of2-formyl-4-isopropylphenyltrifluoromethanesulfonate (white crystal) wasobtained (yield: 75%). Subsequently, under an atmospheric argon gasflow, 2-formyl-4-isopropylphenyl trifluoromethanesulfonate in an amountof 5.9 g (20 mmol), 6-isopropylnaphthalene-2-boronic acid in an amountof 4.7 g (22 mmol), (tetrakistriphenylphosphine)palladium in an amountof 1.1 g (1 mmol), 2N sodium carbonate aqueous solution in an amount of30 milliliter and dimethoxyethane in an amount of 40 milliliter wereplaced into a three necked-flask equipped with a cooling pipe and havinga capacity of 500 milliliter, and the resultant solution was refluxedunder heating for 8 hours. After the reaction terminated, adding waterin an amount of 100 milliliter into the reacted solution, an organiclayer was separated and washed with the use of sodium chloride solution,followed by drying with the use of magnesium sulfate. After removing thesolvent by distillation by means of a rotary evaporator, the resultantcrude product was refined by means of column chromatography (silicagel,hexane/dichloromethane=60/40), and as a result, 4.4 g of an aimedcompound (white crystal) was obtained (yield: 70%).

(3-4) Synthesis of2-isopropyl-6-(4-isopropyl-2-(2-methoxyvinyl)phenyl)naphthalene

Under an atmospheric argon gas flow,5-isopropyl-2-(6-isopropyl-2-naphthyl)benzaldehyde in an amount of 4.4 g(14 mmol), (methoxymethyl)triphenylphosphoniumchloride in an amount of5.1 g (15 mmol), t-butoxypotassium in an amount of 1.7 g (15 mmol) anddesiccated tetrahydrofuran in an amount of 100 milliliter were placedinto a three-necked flask equipped with a cooling pipe and having acapacity of 500 milliliter, and the resultant solution was stirred underheating at the room temperature for one night. After the reactionterminated, adding water in an amount of 100 milliliter into the reactedsolution, an organic layer was separated, followed by drying with theuse of magnesium sulfate. After removing the solvent by distillation bymeans of a rotary evaporator, the resultant crude product was refined bymeans of column chromatography (silicagel,hexane/dichloromethane=10/90), and as a result, 4.3 g of an aimedcompound (white crystal) was obtained (yield: 90%).

(3-5) Synthesis of 2,8-diisopropyl chrysene

Under an atmospheric argon gas flow,2-isopropyl-6-(4-isopropyl-2-(2-methoxy vinyl)phenyl)naphthalene in anamount of 4.3 g (12 mmol), several drops of methyl acid, and desiccateddichloromethane in an amount of 50 milliliter were placed into a threenecked-flask equipped with a cooling pipe and having a capacity of 300milliliter, and the resultant solution was stirred at the roomtemperature for 8 hours. After the reaction terminated, adding sodiumbicarbonate solution in an amount of 100 milliliter into the reactedsolution, crystals were separated by filtration. The resultant crudeproduct was washed with the use of water and methanol, and then, it wasvacuum dried at the temperature of 50° C. for 8 hours, and as a result,3.5 g of an aimed compound (white crystal) was obtained (yield: 90%).

(3-6) Synthesis of 2,8-diisopropyl-6,12-dibromochrysene

Under an atmospheric argon gas flow, 2,8-diisopropyl chrysene in anamount of 3.5 g (12 mmol), N-bromosuccinimide in an amount of 5.3 g (30mmol) and N,N-dimethylformamide in an amount of 20 milliliter wereplaced into a three-neck flask equipped with a cooling pipe and having acapacity of 500 milliliter, and the resultant solution was stirred atthe room temperature for one night. After the reaction terminated,adding water in an amount of 300 milliliter into the reacted solution,crystals were separated by filtration. The resultant crude product waswashed with the use of water and methanol, and then, it wasre-crystallized in 100 milliliter of toluene, and as a result, 4.7 g ofan aimed compound (white crystal) was obtained (yield: 80%).

(3-7) Synthesis of Chemical Compound (20)

Under an atmospheric argon gas flow,2,8-diisopropyl-6,12-dibromochrysene in an amount of 4.7 g (10 mmol),4-isopropylphenyl-p-tolyl amine in an amount of 5.6 g (25 mmol),palladium acetate in an amount of 0.03 g (1.5% by mol),tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliterwere placed into a three-neck flask equipped with a cooling pipe andhaving a capacity of 300 milliliter, and the resultant solution wasstirred under heating at a temperature of 100° C. for one night. Afterthe reaction terminated, precipitated crystals were separated byfiltration and washed with the use of 50 milliliter of toluene and 100milliliter of methanol, and as a result, 6.6 g of pale yellow powderswere obtained. The obtained product was identified to be Compound (20)in accordance with FD-MS measurement (yield: 88%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (20) is shown inFIG. 3. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (20) among the toluene solvent were407 nm and 450 nm respectively.

Synthesis Example 4 Synthesis of Compound (23)

(4-1) Synthesis of 2-t-butyl-8-isopropyl-6,12-dibromochrysene

An aimed compound was obtained in a similar manner as Synthesis Example3 from the step (3-1) to the step (3-6) except that 2-hydroxy-5-t-butylbenzaldehyde was employed instead of 2-hydroxy-5-isopropyl benzaldehydein the step (3-3).

(4-2) Synthesis of Compound (23)

Under an atmospheric argon gas flow, 2-t-butyl-8-isopropyl-6,12-dibromochrysene in an amount of 4.8 g (10 mmol), bis(3,4-dimethylphenyl)aminein an amount of 5.6 g (25 mmol), palladium acetate in an amount of 0.03g (1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxysodium in an amount of 2.4 g (25 mmol) and desiccated toluene in anamount of 100 milliliter were placed into a three-neck flask equippedwith a cooling pipe and having a capacity of 300 milliliter, and theresultant solution was stirred under heating at a temperature of 100° C.for one night. After the reaction terminated, precipitated crystals wereseparated by filtration and washed with the use of 50 milliliter oftoluen and 100 milliliter of methanol, and as a result, 6.9 g of paleyellow powders were obtained. The obtained product was identified to beCompound (23) in accordance with FD-MS measurement (yield: 90%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of 1H-NMR spectrum about the resultant Compound (23) is shown inFIG. 4. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (23) among the toluene solvent were409 nm and 453 nm respectively.

Synthesis Example 5 Synthesis of Compound (25)

Under an atmospheric argon gas flow, 2-isopropyl-6,12-dibromo chryseneobtained in the step (2-1) in Synthesis Example 2 in an amount of 4.2 g(10 mmol), bis(3,4-dimethylphenyl)amine in an amount of 6.3 g (25 mmol),palladium acetate in an amount of 0.03 g (1.5% by mol),tri-t-butylphosphine in an amount of 0.06 g (3% by mol), t-butoxy sodiumin an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of100 milliliter were placed into a three-neck flask equipped with acooling pipe and having a capacity of 300 milliliter, and the resultantsolution was stirred under heating at a temperature of 100° C. for onenight. After the reaction terminated, precipitated crystals wereseparated by filtration and washed with the use of 50 milliliter oftoluen and 100 milliliter of methanol, and as a result, 6.8 g of paleyellow powders were obtained. The obtained product was identified to beCompound (25) in accordance with FD-MS measurement (yield: 88%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (25) is shown inFIG. 5. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (25) among the toluene solvent were415 nm and 459 nm respectively.

Synthesis Example 6 Synthesis of Compound (39)

Under an atmospheric argon gas flow, 2-isopropyl-6,12-dibromo chryseneobtained in the step (2-1) in Synthesis Example 2 in an amount of 4.2 g(10 mmol), di(2-naphthyl)amine in an amount of 6.7 g (25 mmol),palladium acetate in an amount of 0.03 g (1.5% by mol),tri-t-butylphosphine in an amount of 0.06 g (3% by mol), t-butoxy sodiumin an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of100 milliliter were placed into a three-neck flask equipped with acooling pipe and having a capacity of 300 milliliter, and the resultantsolution was stirred under heating at a temperature of 100° C. for onenight. After the reaction terminated, precipitated crystals wereseparated by filtration and washed with the use of 50 milliliter oftoluene and 100 milliliter of methanol, and as a result, 6.8 g of paleyellow powders were obtained. The obtained product was identified to beCompound (39) in accordance with FD-MS measurement (yield: 85%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (39) is shown inFIG. 6. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (39) among the toluene solvent were408 nm and 452 nm respectively.

Synthesis Example 7 Synthesis of Compound (57)

(7-1) Synthesis of 2-t-butyl-6,12-dibromochrysene

An aimed compound was obtained in a similar manner as Synthesis Example1 from the step (1-1) to the step (1-5) except that t-butyl magnesiumbromide was employed instead of methyl magnesium bromide in the step(1-1).

(7-2) Synthesis of Chemical Compound (57)

Under an atmospheric argon gas flow, 2-t-butyl-6,12-dibromochrysene inan amount of 4.4 g (10 mmol), bis(3,4-dimethylphenyl)amine in an amountof 5.6 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% bymol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in anamount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100milliliter were placed into a three-neck flask equipped with a coolingpipe and having a capacity of 300 milliliter, and the resultant solutionwas stirred under heating at a temperature of 100° C. for one night.After the reaction terminated, precipitated crystals were separated byfiltration and washed with the use of 50 milliliter of toluene and 100milliliter of methanol, and as a result, 6.5 g of pale yellow powderswere obtained. The obtained product was identified to be Compound (57)in accordance with FD-MS measurement (yield: 90%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (57) is shown inFIG. 7. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (57) among the toluene solvent were410 nm and 456 nm respectively.

Synthesis Example 8 Synthesis of Compound (95)

Under an atmospheric argon gas flow, 2-methyl-6,12-dibromochryseneobtained in the step (1-5) in Synthesis Example 1 in an amount of 4.0 g(10 mmol), di(4-cyclohexylphenyl)amine in an amount of 8.3 g (25 mmol),palladium acetate in an amount of 0.03 g (1.5% by mol),tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliterwere placed into a three-neck flask equipped with a cooling pipe andhaving a capacity of 300 milliliter, and the resultant solution wasstirred under heating at a temperature of 100° C. for one night. Afterthe reaction terminated, precipitated crystals were separated byfiltration and washed with the use of 50 milliliter of toluene and 100milliliter of methanol, and as a result, 6.3 g of pale yellow powderswere obtained. The obtained product was identified to be Compound (95)in accordance with FD-MS measurement yield: 70%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (95) is shown inFIG. 8. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (95) among the toluene solvent were406 nm and 454 nm respectively.

Synthesis Example 9 Synthesis of Compound (D-973)

Under an atmospheric argon gas flow, 6,12-dibromochrysene in an amountof 3.8 g (10 mmol), N-methylaniline in an amount of 2.7 g (25 mmol,palladium acetate in an amount of 0.03 g (1.5% by mol),tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliterwere placed into a three-necked flask equipped with a cooling pipe andhaving a capacity of 300 milliliter, and the resultant solution wasstirred under heating at a temperature of 100° C. for one night. Afterthe reaction terminated, precipitated crystals were separated byfiltration and washed with the use of 50 milliliter of toluene and 100milliliter of methanol, and as a result, 2.2 g of white powders wereobtained. The obtained product was identified to be Compound (D-973) inaccordance with FD-MS measurement (yield: 50%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (D-973) is shownin FIG. 9. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (D-973) among the toluene solventwere 373 nm and 440 nm respectively.

Synthesis Example 10 Synthesis of Compound (D-974)

Under an atmospheric argon gas flow, 6,12-dibromochrysene in an amountof 3.8 g (10 mmol), N-isopropylaniline in an amount of 3.4 g (25 mmol,palladium acetate in an amount of 0.03 g (1.5% by mol),tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in an amount of2.4 g (25 mmol) and desiccated toluene in an amount of 100 milliliterwere placed into a three-neck flask equipped with a cooling pipe andhaving a capacity of 300 milliliter, and the resultant solution wasstirred under heating at a temperature of 100° C. for one night. Afterthe reaction terminated, precipitated crystals were separated byfiltration and washed with the use of 50 milliliter of toluene and 100milliliter of methanol, and as a result, 2.0 g of pale yellow powderswere obtained. The obtained product was identified to be Compound(C-974) in accordance with FD-MS measurement (yield: 40%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (D-974) is shownin FIG. 10. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (D-974) among the toluene solventwere 362 nm and 436 nm respectively.

Synthesis Example 11 Synthesis of Compound (D-998)

Under an atmospheric argon gas flow, 6,12-dibromochrysene in an amountof 3.8 g (10 mmol), N-(4-isopropylphenyl)pyridine-3-amine in an amountof 5.3 g (25 mmol), palladium acetate in an amount of 0.03 g (1.5% bymol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodium in anamount of 2.4 g (25 mmol) and desiccated toluene in an amount of 100milliliter were placed into a three-neck flask equipped with a coolingpipe and having a capacity of 300 milliliter, and the resultant solutionwas stirred under heating at a temperature of 100° C. for one night.After the reaction terminated, precipitated crystals were separated byfiltration and washed with the use of 50 milliliter of toluene and 100milliliter of methanol, and as a result, 4.2 g of pale yellow powderswere obtained. The obtained product was identified to be Compound(D-998) in accordance with FD-MS measurement (yield: 65%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (D-998) is shownin FIG. 11. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (D-998) among the toluene solventwere 393 nm and 444 nm respectively.

Synthesis Example 12 Synthesis of Compound (D-1000)

Under an atmospheric argon gas flow, 2-methyl-6,12-dibromochrysene in anamount of 3.9 g (10 mmol), N-(4-isopropylphenyl)pyridine-3-amine in anamount of 5.3 g (25 mmol), palladium acetate in an amount of 0.03 g(1.5% by mol), tri-t-butylphosphine 0.06 g (3% by mol), t-butoxy sodiumin an amount of 2.4 g (25 mmol) and desiccated toluene in an amount of100 milliliter were placed into a three-neck flask equipped with acooling pipe and having a capacity of 300 milliliter, and the resultantsolution was stirred under heating at a temperature of 100° C. for onenight. After the reaction terminated, precipitated crystals wereseparated by filtration and washed with the use of 50 milliliter oftoluene and 100 milliliter of methanol, and as a result, 5.3 g of paleyellow powders were obtained. The obtained product was identified to beCompound (D-1000) in accordance with FD-MS measurement (yield: 80%).

Measurement by means of DRX-500 (Trade name; produced by Brucker OpticsInc.) was carried out using dimethylene chloride as a solvent and aresult of ¹H-NMR spectrum about the resultant Compound (D-1000) is shownin FIG. 12. Further, the maximum absorption wavelength and the maximumfluorescence wavelength of Compound (D-1000) among the toluene solventwere 385 nm and 440 nm respectively.

Example 1

A 120 nm-thick transparent electrode made of indium oxide was formed ona glass substrate having a size of 25 mm×75 mm×1.1 mm. The glasssubstrate with the transparent electrode was cleaned by irradiation ofUltra Violet ray and ozone. The thus cleaned glass substrate with thetransparent electrode was mounted to a vacuum vapor depositionapparatus.

First,N′,N″-bis[4-(diphenylamino)phenyl]-N′,N″-diphenylbiphenyl-4,4′-diaminewas vapor-deposited to form a hole injecting layer having a thickness of60 nm, and then N,N,N′,N′-tetrakis(4-biphenyl)-4,4′-bendizine was vapordeposited on the hole injecting layer to form a hole transporting layerhaving a thickness of 20 nm. Then,10,10′-bis[1,1′,4′,1″]terphenyl-2-yl-9,9′-bianthracenyl and the aboveCompound (9) were simultaneously vapor deposited at a weight ratio of40:2 on the hole transporting layer to form a light emitting layerhaving a thickness of 40 nm.

Next, tris(8-hydroxyquinolinato)aluminum was vapor-deposited on thelight emitting layer to form an electron injecting layer having athickness of 10 nm. Then, tris(8-hydroxyquinolinato)aluminum and lithiumwas vapor-deposited at a weight ratio of 10:0.3 on the electroninjecting layer to form a layer having a thickness of 10 nm, and furtheraluminum was vapor-deposited thereon to form an aluminum layer having athickness of 150 nm. The aluminum layer functioned as a cathode. Thus,an organic EL device was fabricated.

As a result of subjecting the thus obtained organic EL device to a testby passing electric current, it was confirmed that a blue light with aluminance of 602 cd/m² (peak wavelength of light emission: 464 nm) andcurrent efficiency of 6.0 cd/A was emitted at a voltage of 6.0 V and acurrent density of 10 mA/cm². Further, as a result of subjecting thedevice to a continuous test by passing DC electric current starting atan initial luminance of 500 cd/m², it was confirmed that the halflifetime thereof was 18900 hours.

Example 2

An organic EL device was fabricated in accordance with the sameprocedures as those conducted in Example 1 except that Compound (9) wasreplaced with Compound (23).

As a result of subjecting the thus obtained organic EL device to a testby passing electric current, it was confirmed that a blue light with aluminance of 664 cd/m² (peak wavelength of light emission: 462 nm) andcurrent efficiency of 6.6 cd/A was emitted at a voltage of 6.5 V and acurrent density of 10 mA/cm². Further, as a result of subjecting thedevice to a continuous test by passing DC electric current starting atan initial luminance of 500 cd/m², it was confirmed that the halflifetime thereof was 16000 hours.

Example 3

An organic EL device was fabricated in accordance with the sameprocedures as those conducted in Example 1 except that10,10′-bis[1,1′,4′,1′]terphenyl-2-yl-9,9′-bianthracenyl was replacedwith 10-(3-(naphthalen-1-yl)phenyl)-9-(naphthalen-2-yl)anthracene.

As a result of subjecting the thus obtained organic EL device to a testby passing electric current, it was confirmed that a blue light with aluminance of 631 cd/m² (peak wavelength of light emission: 464 nm) andcurrent efficiency of 6.3 cd/A was emitted at a voltage of 6.5 V and acurrent density of 10 mA/cm². Further, as a result of subjecting thedevice to a continuous test by passing DC electric current starting atan initial luminance of 500 cd/m², it was confirmed that the halflifetime thereof was 20000 hours or longer.

Example 4

An organic EL device was fabricated in accordance with the sameprocedures as those conducted in Example 3 except that Compound (9) wasreplaced with Compound (23) for the doping material.

As a result of subjecting the thus obtained organic EL device to a testby passing electric current, it was confirmed that a blue light with aluminance of 710 cd/m² (peak wavelength of light emission: 465 nm) andcurrent efficiency of 7.1 cd/A was emitted at a voltage of 6.5 V and acurrent density of 10 mA/cm². Further, as a result of subjecting thedevice to a continuous test by passing DC electric current starting atan initial luminance of 500 cd/m², it was confirmed that the halflifetime thereof was 20000 hours or longer.

Example 5

An organic EL device was fabricated in accordance with the sameprocedures as those conducted in Example 3 except that Compound (9) wasreplaced with Compound (25) for the doping material.

As a result of subjecting the thus obtained organic EL device to a testby passing electric current, it was confirmed that a blue light with aluminance of 793 cd/m² (peak wavelength of light emission: 469 nm) andcurrent efficiency of 7.9 cd/A was emitted at a voltage of 6.5 V and acurrent density of 10 mA/cm². Further, as a result of subjecting thedevice to a continuous test by passing DC electric current starting atan initial luminance of 500 cd/m², it was confirmed that the halflifetime thereof was 20000 hours or longer.

Example 6

An organic EL device was fabricated in accordance with the sameprocedures as those conducted in Example 3 except that Compound (9) wasreplaced with Compound (10) for the doping material.

As a result of subjecting the thus obtained organic EL device to a testby passing electric current, it was confirmed that a blue light with aluminance of 782 cd/m² (peak wavelength of light emission: 468 nm) andcurrent efficiency of 7.8 cd/A was emitted at a voltage of 6.5 V and acurrent density of 10 mA/cm². Further, as a result of subjecting thedevice to a continuous test by passing DC electric current starting atan initial luminance of 500 cd/m², it was confirmed that the halflifetime thereof was 20000 hours or longer.

Comparative Example 1

An organic EL device was fabricated in accordance with the sameprocedures as those conducted in Example 1 except that Compound (9) wasreplaced with 6,12-bis(4-isopropylphenyl-p-tolylamino)chrysene.

As a result of subjecting the thus obtained organic EL device to a testby passing electric current, it was confirmed that a blue light with aluminance of 594 cd/m² (peak wavelength of light emission: 462 nm) andcurrent efficiency of 5.9 cd/A was emitted at a voltage of 6.3 V and acurrent density of 10 mA/cm². Further, as a result of subjecting thedevice to a continuous test by passing DC electric current starting atan initial luminance of 500 cd/m², it was confirmed that the halflifetime thereof was 4590 hours.

From the above-mentioned result, it is apparent that when anysubstituent does not bond to diaminochrysene backbone structure, halflifetime shortens because of an association between compounds eachother.

INDUSTRIAL APPLICABILITY

The organic EL device using the aromatic amine derivative according tothe present invention can exhibit a practically sufficient luminance oflight emission even upon applying a low voltage thereto, and has anenhanced efficiency of light emission and the device is free fromdeterioration in properties even after being used for a long period oftime and, therefore, has a long lifetime. Resultantly, the EL device isuseful as a flat panel light emitting member for a wall-hanging typetelevision or as a light source of backlight and the like for displaydevices.

1. An aromatic amine derivative represented by the following generalformula (1):

wherein A₁ to A₄ each independently represents a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted aryl group having 5 to 50 ring carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 50 ringcarbon atoms, a substituted or unsubstituted cycloalkyl group having 3to 50 ring carbon atoms, a substituted or unsubstituted alkoxyl grouphaving 1 to 50 ring carbon atoms, a substituted or unsubstituted aryloxygroup having 5 to 50 ring carbon atoms, a substituted or unsubstitutedarylamino group having 5 to 50 ring carbon atoms, a substituted orunsubstituted alkylamino group having 1 to 20 carbon atoms, asubstituted or unsubstituted heterocyclic group having 3 to 50 ringcarbon atoms, a substituted or unsubstituted silyl group having 3 to 50carbon atoms or a halogen atom; a, b, c and d each independentlyrepresents an integer of 0 to 5, when a, b, c or d each is 2 or greater,A₁ to A₄ may be the same with or different from each other, and may bondeach other to form a saturated or unsaturated ring; and further, acouple of A₁ and A₂, and a couple of A₃ and A₄ may bond each other toform a saturated or unsaturated ring; R₁ to R₄ each independentlyrepresents a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted aryl grouphaving 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkylgroup having 6 to 50 ring carbon atoms, a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms, a substituted orunsubstituted arylamino group having 5 to 20 ring carbon atoms, asubstituted or unsubstituted alkylamino group having 1 to 20 carbonatoms, a substituted or unsubstituted heterocyclic group having 3 to 50ring carbon atoms or a substituted or unsubstituted silyl group having 3to 50 carbon atoms; a couple of R₁ and R₂, and a couple of R₃ and R₄ maybond each other to form a saturated or unsaturated ring; however, a casewhere all of R₁ to R₄ in the general formula (1) are hydrogen atoms isexcluded.
 2. The aromatic amine derivative according to claim 1, whereinat least one of R₁ or R₃ in the general formula (1) independentlyrepresents a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted aryl group having 5 to 50ring carbon atoms, a substituted or unsubstituted aralkyl group having 6to 50 ring carbon atoms or a substituted or unsubstituted cycloalkylgroup having 3 to 50 ring carbon atoms.
 3. The aromatic amine derivativeaccording to claim 1, wherein R₁ and R₃ in the general formula (1) eachindependently represents a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted aryl grouphaving 5 to 50 ring carbon atoms, a substituted or unsubstituted aralkylgroup having 6 to 50 ring carbon atoms or a substituted or unsubstitutedcycloalkyl group having 3 to 50 ring carbon atoms.
 4. The aromatic aminederivative according to claim 1, wherein at least one of R₂ or R₄ in thegeneral formula (1) independently represents a substituted orunsubstituted primary alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted secondary alkyl group having 1 to 50 carbonatoms, a substituted or unsubstituted aryl group having 5 to 50 ringcarbon atoms, a substituted or unsubstituted aralkyl group having 1 to50 ring carbon atoms or a substituted or unsubstituted cycloalkyl grouphaving 3 to 50 ring carbon atoms.
 5. The aromatic amine derivativeaccording to claim 1, wherein R₁ to R₄ in the general formula (1) eachindependently represents a hydrogen atom, a substituted or unsubstitutedarylamino group having 5 to 20 ring carbon atoms, a substituted orunsubstituted alkylamino group having 1 to 20 carbon atoms, asubstituted or unsubstituted heterocyclic group having 3 to 50 ringcarbon atoms or a substituted or unsubstituted silyl group having 3 to50 carbon atoms.
 6. The aromatic amine derivative according to claim 1,wherein A₁ to A₄ each independently represents a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 5 to 20 ring carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 20 ringcarbon atoms, a substituted or unsubstituted cycloalkyl group having 5to 12 ring carbon atoms, a substituted or unsubstituted alkoxyl grouphaving 1 to 6 ring carbon atoms, a substituted or unsubstituted aryloxygroup having 5 to 18 ring carbon atoms, a substituted or unsubstitutedarylamino group having 5 to 18 ring carbon atoms, a substituted orunsubstituted alkylamino group having 1 to 6 carbon atoms, a substitutedor unsubstituted heterocyclic group having 3 to 20 ring carbon atoms, asubstituted or unsubstituted silyl group having 3 to 20 carbon atoms ora halogen atom; a, b, c and d each independently represents an integerof 0 to 2, when a, b, c or d each is 2 or greater, A₁ to A₄ may be thesame with or different from each other, and may bond each other to forma saturated or unsaturated ring; and further, a couple of A₁ and A₂, anda couple of A₃ and A₄ may bond each other to form a saturated orunsaturated ring; R₁ to R₄ each independently represents a hydrogenatom, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted aryl group having 5 to 20 ringcarbon atoms, a substituted or unsubstituted aralkyl group having 6 to20 ring carbon atoms, a substituted or unsubstituted cycloalkyl grouphaving 5 to 12 ring carbon atoms, a substituted or unsubstitutedarylamino group having 5 to 18 ring carbon atoms, a substituted orunsubstituted alkylamino group having 1 to 10 carbon atoms, asubstituted or unsubstituted heterocyclic group having 3 to 20 ringcarbon atoms or a substituted or unsubstituted silyl group having 3 to20 carbon atoms; a couple of R₁ and R₂, and a couple of R₃ and R₄ maybond each other to form a saturated or unsaturated ring; however, a casewhere all of R₁ to R₄ in the general formula (1) are hydrogen atoms isexcluded.
 7. The aromatic amine derivative according to claim 1, whereinthe alkyl group represented by R₂ and R₄ in the general formula (1) areprimary or secondary.
 8. The aromatic amine derivative according toclaim 1, wherein at least one of R₁ or R₃ in the general formula (1)represents a methyl group, an ethyl group, a propyl group, an isopropylgroup, a butyl group, a s-butyl group, a t-butyl group or a cyclohexylgroup.
 9. The aromatic amine derivative according to claim 1, wherein atleast one of R₂ or R₄ in the general formula (1) represents a methylgroup, an ethyl group, a propyl group, an isopropyl group, a butylgroup, a s-butyl group, a t-butyl group or a cyclohexyl group.
 10. Thearomatic amine derivative according to claim 1, which is represented bythe following formula:


11. The aromatic amine derivative according to claim 1, which isrepresented by the following formula:


12. The aromatic amine derivative according to claim 1, which isrepresented by the following formula:


13. The aromatic amine derivative according to claim 1, which isrepresented by the following formula:


14. The aromatic amine derivative according to claim 1, which isrepresented by the following formula:


15. The aromatic amine derivative according to claim 1, which isrepresented by the following formula:


16. The aromatic amine derivative according to claim 1, which isrepresented by the following formula:


17. The aromatic amine derivative according to claim 1, which isrepresented by the following formula: